Diisopropylethylamine → 2-(2-Chloro-5-methylpyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid [bis-(4-methoxyphenyl)-methyl]-amide

HRID 1986309Notes

Reaction equation

HRID 1986309 reaction equation
C(N(C(C)C)CC)(C)C.[Cl:10][C:11]1[N:16]=[C:15]([C:17]2[S:21][C:20]3[CH:22]=[CH:23][CH:24]=[C:25]([C:26]([OH:28])=O)[C:19]=3[CH:18]=2)[C:14]([CH3:29])=[CH:13][N:12]=1.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]([NH2:47])[C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)=[CH:34][CH:33]=1.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.C(OCC)C>[CH3:46][O:45][C:42]1[CH:41]=[CH:40][C:39]([CH:38]([NH:47][C:26]([C:25]2[C:19]3[CH:18]=[C:17]([C:15]4[C:14]([CH3:29])=[CH:13][N:12]=[C:11]([Cl:10])[N:16]=4)[S:21][C:20]=3[CH:22]=[CH:23][CH:24]=2)=[O:28])[C:35]2[CH:36]=[CH:37][C:32]([O:31][CH3:30])=[CH:33][CH:34]=2)=[CH:44][CH:43]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 3500424,4'-DimethoxybenzhydrylamineHCID 866253892-(2-Chloro-5-methylpyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid

Product 1

HCID 866253592-(2-Chloro-5-methylpyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid [bis-(4-methoxyphenyl)-methyl]-amideYield 99.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Diisopropylethylamine (1.80 mL, 10.3 mmol) is added to a stirred suspension of 2-(2-chloro-5-methylpyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid (3.00 g, 9.84 mmol) in anhydrous dichloromethane (100 mL) at 0° C. under nitrogen to form a solution, then followed by the successive addition of C,C-bis-(4-methoxyphenyl)-methylamine (2.51 g, 10.3 mmol) and powdered 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (4.56 g, 10.3 mmol). The resultant mixture is allowed to stir at 0° C. for 1 hour, then at room temperature for 3 hours. Diethyl ether (50 mL) is added in small portions to the mixture, the mixture is stirred for another 10 minutes before filtration. After vacuum drying at 35° C., the crude title compound (5.19 g) is obtained as a tan solid. It is used without further purification.

Workup

  1. customto form a solution
  2. waitat room temperature for 3 hours
  3. stirringthe mixture is stirred for another 10 minutes before filtration
  4. customAfter vacuum drying at 35° C.

Sources & evidence

ORD record
ord-66a12267fd2c4f648b98d56e4c2e0f19
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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