Triethylamine → HCID 59304969, compound

HRID 1958602Notes

Reaction equation

HRID 1958602 reaction equation
C(OC([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[N:24][C:23]([NH:26][CH2:27][C:28]3[CH:37]=[CH:36][C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH:29]=3)=[CH:22][N:21]=2)=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=O)(C)(C)C.O[CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>ClCCl>[NH2:8][C@@H:9]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:25]=[N:24][C:23]([NH:26][CH2:27][C:28]3[CH:37]=[CH:36][C:31]4[C:30](=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH:29]=3)=[CH:22][N:21]=2)=[CH:18][CH:19]=1)[C:10]([O:12][CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1)=[O:11]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 611632-MorpholinoethanolHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate2×HCID 59304962HCID 59304962, compound

Product 1

HCID 59304969HCID 59304969, compoundYield 4.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-(Tert-butoxycarbonylamino)-3-(4-(5-(naphthalen-2-ylmethylamino)pyrazin-2-yl)phenyl)propanoic acid (48 mg, 0.090 mmol), 4-(2-hydroxyethyl)morpholine (12 mg, 0.090 mmol), triethylamine (18 mg, 0.180 mmol), and benzotriazole-1-yloxytris(dimethylamino)-phosphonium hexaflurophosphate (BOP, 18 mg, 0.090 mmol), in dichloromethane (3.0 ml) were stirred at room temperature for 5 hours. Additional triethylamine (18 mg, 0.180 mmol) and BOP (18 mg, 0.090 mmol) were added, and the mixture was stirred overnight. The mixture was concentrated and purified via prep HPLC to give 2 mg of the captioned compound.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified via prep HPLC

Sources & evidence

ORD record
ord-ef43cb4be2854354aa4b56d2d9db22db
Source dataset
uspto-grants-2013_04
Patent number
US08410121B2

Reaction notes

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