Hydrochloric Acid → HCID 72943390, compound

HRID 531525Notes

Reaction equation

HRID 531525 reaction equation
[F:1][C:2]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:3]=1[CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:20]=[C:21]([N:25]5[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]5)[CH:22]=[CH:23][CH:24]=4)[CH:17]=3)[NH:12][CH:11]=2)[CH:7]=[N:6]1.Cl.CCOCC>CO.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:3]=1[CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N:25]5[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]5)[CH:20]=4)[CH:17]=3)[NH:12][CH:11]=2)[CH:7]=[N:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 90031370HCID 90031370, compound

Product 1

HCID 72943390HCID 72943390, compoundYield 9.75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

To a stirred solution of tert-butyl 4-(3-(3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (Example-31) (200 mg, 0.351 mmol) in methanol (5 ml) added saturated HCl in methanol at 0° C. This gradually brought to RT and stirred for four hours. Reaction mass was cooled and added ether to get solids. Solvents decanted and solids washed by ethyl acetate and dried. This residue was made free base using saturated sodium carbonate. This afforded 16.0 mg (9.75% yield) of titled compound after purification by preparative TLC (SiO2 using 3% methanol in chloroform as eluent). 1H NMR (CD3OD, 300 MHz): δ 8.557-8.550 (d, 1H), 8.192-8.184 (d, 1H), 7.866 (s, 1H), 7.762 (s, 1H), 7.446-7.360 (m, 2H), 7.160-7.10 (m, 2H), 7.05-6.85 (m, 3H), 5.420 (s, 2H), 3.276-3.242 (m, 4H), 3.119-3.086 (m, 4H). MS: m/z=470.9 (M+1); HPLC: 97.41% in method A.

Workup

  1. customThis gradually brought to RT
  2. customReaction mass
  3. temperaturewas cooled
  4. customto get solids
  5. customSolvents decanted
  6. washsolids washed by ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-492f2f1165bc43cbac7a8c3e30122054
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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