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Trifluoroacetic acid → HCID 59471847, compound

HRID 2204853
Notes
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Reaction equation

HRID 2204853 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[N:10]=[CH:11][C:12]([C:26]2[CH:47]=[CH:46][C:29]([C:30]([N:32]3[CH2:38][CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]3)=[O:31])=[CH:28][C:27]=2[C:48]#[N:49])=[N:13][C:14]=1[C:15]1[O:16][C:17]([C:20]2[S:21][CH:22]=[CH:23][C:24]=2[CH3:25])=[N:18][N:19]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.C(#N)C.CO>[NH2:8][C:9]1[N:10]=[CH:11][C:12]([C:26]2[CH:47]=[CH:46][C:29]([C:30]([N:32]3[CH2:38][CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)=[O:31])=[CH:28][C:27]=2[C:48]#[N:49])=[N:13][C:14]=1[C:15]1[O:16][C:17]([C:20]2[S:21][CH:22]=[CH:23][C:24]=2[CH3:25])=[N:18][N:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 59472333HCID 59472333, compound

Product 1

HCID 59471847HCID 59471847, compoundYield 43.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

tert-Butyl 4-[4-[5-[bis(tert-butoxycarbonyl)amino]-6-[5-(3-methyl-2-thienyl)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-3-cyano-benzoyl]-1,4-diazepane-1-carboxylate (9.9 g, 11.32 mmol) was dissolved in anhydrous CH2Cl2 (100 mL) at room temperature and TFA (10 mL, 129.8 mmol) added. Additional TFA (10 mL, 129.8 mmol) was added and the reaction mixture stirred at room temperature for 3.5 h and then concentrated in vacuo. The material was dissolved in a mixture of acetonitrile and methanol (10; 1 mixture) and PS—HCO3 (5 eq) added. The mixture was stirred for 1 h at room temperature and then the resin removed by filtration and washed with acetonitrile and methanol. The filtrate was concentrated in vacuo and the residue recrystallised from acetonitrile. The isolated solid was washed with ether and dried to give the product as a yellow solid (2.41 g, 35% yield); 1H NMR (400 MHz, DMSO) d 1.76-1.84 (m, 2H), 2.67 (s, 3H), 2.88-2.93 (m, 4H), 3.42-3.44 (m, 2H), 3.67-3.74 (m, 2H), 7.2 (d, 1H), 7.84-7.87 (m, 1H), 7.89-7.99 (m, 1H), 8.04-8.09 (m, 2H) and 8.85 (s, 1H) ppm; MS (ES+) 487.26

Workup

  1. concentrationconcentrated in vacuo
  2. additionadded
  3. stirringThe mixture was stirred for 1 h at room temperature
  4. customthe resin removed by filtration
  5. washwashed with acetonitrile and methanol
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue recrystallised from acetonitrile
  8. washThe isolated solid was washed with ether
  9. customdried

Sources & evidence

ORD record
ord-60613701dde249c6be1f1ffe43cd767a
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09365557B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes