Triethylamine → HCID 58904518, compound

HRID 1292751Notes

Reaction equation

HRID 1292751 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:9][C@@H:10]([C@@:14]2([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[NH:20][CH2:19][C:18](=[O:21])[N:17]([CH2:22][C:23]3[C:28]([F:29])=[CH:27][C:26]([F:30])=[CH:25][C:24]=3[F:31])[C:16]3[CH:32]=[CH:33][CH:34]=[CH:35][C:15]2=3)[C:11]([OH:13])=[O:12])[N:3]=1.C(N(CC)CC)C.Cl[CH2:50][C:51]([N:53]([CH3:55])[CH3:54])=[O:52]>CN(C=O)C.CC(=O)OCC>[CH3:54][N:53]([CH3:55])[C:51]([CH2:50][O:12][C:11](=[O:13])[C@@H:10]([O:9][C:4]1[N:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]=1)[C@@:14]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[NH:20][CH2:19][C:18](=[O:21])[N:17]([CH2:22][C:23]2[C:28]([F:29])=[CH:27][C:26]([F:30])=[CH:25][C:24]=2[F:31])[C:16]2[CH:32]=[CH:33][CH:34]=[CH:35][C:15]1=2)=[O:52]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 758862-chloro-N,N-dimethylacetamideHCID 10166543HCID 10166543, compound

Product 1

HCID 58904518HCID 58904518, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (±)-(S*)-(4,6-dimethyl-pyrimidin-2-yloxy)-[(5S*)-2-oxo-5-phenyl-1-(2,4,6-trifluoro-benzyl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]di-azepin-5-yl]-acetic acid (150 mg, 0.266 mmol, Example 107) in DMF (5 ml) is treated with triethylamine (162 mg, 1.60 mmol) and 2-chloro-dimethylacetamide (162 mg, 1.38 mmol). The mixture is stirred at rt for 18 h before it is diluted with EA, washed twice with water, dried over MgSO4 and evaporated. The crude product is purified by chromatography on prep. tlc plates (DCM with 10% methanol) and crystallisation from diethyl ether/hexane to give (±)-(S*)-(4,6-dimethyl-pyrimidin-2-yloxy)-[(5S*)-2-oxo-5-phenyl-1-(2,4,6-trifluoro-benzyl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl]-acetic acid dimethylcarbamoylmethyl ester (151 mg) as a white powder. LC-MS1: tR=1.10 min, [M+1]+=648.15.

Workup

  1. washwashed twice with water
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe crude product is purified by chromatography on prep
  5. customtlc plates (DCM with 10% methanol) and crystallisation from diethyl ether/hexane

Sources & evidence

ORD record
ord-80972fb185cc4060b585c8ff87ea5358
Source dataset
uspto-grants-2007_07
Patent number
US07238685B2

Reaction notes

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