Diisopropylethylamine → Arylaminoethyl amide deriv. 36

HRID 1783863Notes

Reaction equation

HRID 1783863 reaction equation
[CH2:1]([S:8][CH2:9][C@H:10]([NH:14][C:15]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:16])[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:23][C:24]([F:38])([F:37])[O:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][CH2:33][C@@H:34]([NH2:36])[CH3:35])=[CH:28][CH:27]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:1]([S:8][CH2:9][C@H:10]([NH:14][C:15]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:16])[C:11](=[O:13])[NH:36][C@@H:34]([CH3:35])[CH2:33][NH:32][C:29]1[CH:28]=[CH:27][C:26]([O:25][C:24]([F:23])([F:37])[F:38])=[CH:31][CH:30]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 542379343-Benzylsulfanyl-2-(R)-[(morpholine-4-carbonyl)-amino]-propionic acidHCID 59733160HCID 59733160, compound

Product 1

HCID 11466845Arylaminoethyl amide deriv. 36Yield 6.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Benzylsulfanyl-2-(R)-[(morpholine-4-carbonyl)-amino]-propionic acid (182 mg, 0.56 mmol, 1.2 eq.), N1-(4-Trifluoromethoxy-phenyl)-(S)-propane-1,2-diamine from Scheme 1a (110 mg, 0.47 mmol, 1.0 eq.), and HATU (185 mg, 0.56 mmol, 1.2 eq.) were dissolved in CH2Cl2 (2 mL) at room temperature. DIPEA (245 μL, 1.41 mmol, 3.0 eq.) was added via syringe and the resulting mixture was monitored by LC/MS to completion. After the reaction was complete, the solvent was evaporated and directly purified by mass-directed HPLC and provided 22 mg (0.03 mmol, 5%) of a off-white solid (mono-TFA salt): HPLC-MS calcd. for C25H31F3N4O4S (M+H+) 541.2, found 541.3.

Workup

  1. customthe solvent was evaporated
  2. customdirectly purified by mass-directed HPLC

Sources & evidence

ORD record
ord-1cc77382802c48728c4db5a5d524e272
Source dataset
uspto-grants-2009_03
Patent number
US07501408B2

Reaction notes

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