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

HRID 930980Notes

Reaction equation

HRID 930980 reaction equation
Cl[C:2]1[C:3]2[C:10]3[CH2:11][CH2:12][CH:13]([C:15]([N:17]([CH2:21][CH3:22])[CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:14][C:9]=3[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:23][C:24]1[C:33]([O:34][CH3:35])=[CH:32][C:27]2[NH:28][C:29](=[O:31])[S:30][C:26]=2[CH:25]=1>>[CH2:21]([N:17]([CH:18]([CH3:20])[CH3:19])[C:15]([CH:13]1[CH2:12][CH2:11][C:10]2[C:3]3[C:2]([NH:23][C:24]4[C:33]([O:34][CH3:35])=[CH:32][C:27]5[NH:28][C:29](=[O:31])[S:30][C:26]=5[CH:25]=4)=[N:7][CH:6]=[N:5][C:4]=3[S:8][C:9]=2[CH2:14]1)=[O:16])[CH3:22]

Participants

3

Reactant 2

HCID 90014857(RS)-4-chloro-N-ethyl-N-isopropyl-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 90015179(RS)-N-Ethyl-N-isopropyl-4-[(5-methoxy-2-oxo-2,3-dihydro-1,3-benzothiazol-6-yl)amino]-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxamide

Procedure

40 mg (118 μmol) (RS)-4-chloro-N-ethyl-N-isopropyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxamide (prepared according to intermediate example 86a) 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 10.9 mg (18%) of the title compound.

Workup

  1. customto give
  2. custompurification 10.9 mg (18%) of the title compound

Sources & evidence

ORD record
ord-d5061dd2214c4a6b93cd088a56fede67
Source dataset
uspto-grants-2016_03
Patent number
US09296757B2

Reaction notes

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