(RS)-4-chloro-N-(2-methoxyethyl)-N-propyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxamide → (RS)-N-(2-Methoxyethyl)-4-[(5-methoxy-2-oxo-2,3-dihydro-1,3-benzothiazol-6-yl)amino]-N-propyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxamide

HRID 930982Notes

Reaction equation

HRID 930982 reaction equation
Cl[C:2]1[C:3]2[C:10]3[CH2:11][CH2:12][CH:13]([C:15]([N:17]([CH2:21][CH2:22][O:23][CH3:24])[CH2:18][CH2:19][CH3:20])=[O:16])[CH2:14][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:25][C:26]1[C:35]([O:36][CH3:37])=[CH:34][C:29]2[NH:30][C:31](=[O:33])[S:32][C:28]=2[CH:27]=1>>[CH3:24][O:23][CH2:22][CH2:21][N:17]([CH2:18][CH2:19][CH3:20])[C:15]([CH:13]1[CH2:12][CH2:11][C:10]2[C:3]3[C:2]([NH:25][C:26]4[C:35]([O:36][CH3:37])=[CH:34][C:29]5[NH:30][C:31](=[O:33])[S:32][C:28]=5[CH:27]=4)=[N:7][CH:6]=[N:5][C:4]=3[S:8][C:9]=2[CH2:14]1)=[O:16]

Participants

3

Reactant 2

HCID 90014760(RS)-4-chloro-N-(2-methoxyethyl)-N-propyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxamideHCID 900149486-amino-5-methoxy-1,3-benzothiazol-2(3H)-one

Product 1

HCID 90014625(RS)-N-(2-Methoxyethyl)-4-[(5-methoxy-2-oxo-2,3-dihydro-1,3-benzothiazol-6-yl)amino]-N-propyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxamide

Procedure

100 mg (272 μmol) (RS)-4-chloro-N-(2-methoxyethyl)-N-propyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxamide (prepared according to intermediate example 87a) were transformed in analogy to example 1 using 6-amino-5-methoxy-1,3-benzothiazol-2(3H)-one to give after working up and purification 11.7 mg (8%) of the title compound.

Workup

  1. customto give
  2. custompurification 11.7 mg (8%) of the title compound

Sources & evidence

ORD record
ord-86000390397944168e4345913ab40a7f
Source dataset
uspto-grants-2016_03
Patent number
US09296757B2

Reaction notes

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