Triethylamine → HCID 59822377, compound

HRID 1678464Notes

Reaction equation

HRID 1678464 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:24])=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21](O)=[O:22])=[CH:17][CH:16]=2)[CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:25]=[S:26]1(=[O:40])[CH2:31][CH2:30][N:29]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=2)[CH2:28][CH2:27]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:14]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21](=[O:22])[NH:39][C:36]3[CH:37]=[CH:38][C:33]([CH2:32][N:29]4[CH2:28][CH2:27][S:26](=[O:25])(=[O:40])[CH2:31][CH2:30]4)=[CH:34][CH:35]=3)=[CH:19][CH:20]=2)[C:12]([CH3:24])=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27796824-(4-Aminobenzyl)thiomorpholine 1,1-dioxideHCID 59822348HCID 59822348, compound

Product 1

HCID 59822377HCID 59822377, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5′-tert-butoxycarbonylamino-2′-methyl-biphenyl-4-carboxylic acid (500 mg), 4-(1,1-dioxo-1lambda*6*-thiomorpholin-4-ylmethyl) -phenylamine (367 mg), triethylamine (0.64 ml) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (869 mg) in dry DMF (20 ml) was stirred at 20 C for 118 h. The mixture was then partitioned between water and dichloromethane. The dried extracts were evaporated and the residue purified on silica gel. Elution with ethyl acetate:petrol; 1:1 removed high Rf impurities and further elution with ethyl acetate gave the title compound as a pale yellow solid (693 mg).

Workup

  1. customThe mixture was then partitioned between water and dichloromethane
  2. customThe dried extracts were evaporated
  3. customthe residue purified on silica gel
  4. washElution with ethyl acetate
  5. wash1:1 removed high Rf impurities and further elution with ethyl acetate

Sources & evidence

ORD record
ord-d623748c0af3409d8c06b54dc1b04502
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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