HCID 67263985, compound → HCID 86634038, compound

HRID 1041458Notes

Reaction equation

[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][CH2:5][O:6][C:7]([N:9]1[C:15]2[CH:16]=[CH:17][C:18]([NH2:20])=[CH:19][C:14]=2[O:13][CH2:12][CH2:11][CH2:10]1)=[O:8].[CH2:22]([NH:25][C:26]([C:28]1[S:29][CH:30]=[CH:31][C:32]=1[NH:33][C:34]1[C:39]([Cl:40])=[CH:38][N:37]=[C:36](Cl)[N:35]=1)=[O:27])[C:23]#[CH:24]>>[CH3:21][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]([N:9]1[C:15]2[CH:16]=[CH:17][C:18]([NH:20][C:36]3[N:35]=[C:34]([NH:33][C:32]4[CH:31]=[CH:30][S:29][C:28]=4[C:26](=[O:27])[NH:25][CH2:22][C:23]#[CH:24])[C:39]([Cl:40])=[CH:38][N:37]=3)=[CH:19][C:14]=2[O:13][CH2:12][CH2:11][CH2:10]1)=[O:8]

Participants

Reactant 2

HCID 67263985HCID 67263985, compound

HCID 86634039HCID 86634039, compound

Product 1

HCID 86634038HCID 86634038, compound

Procedure

3-[5-Chloro-4-(2-prop-2-ynylcarbamoyl-thiophen-3-ylamino)-pyrimidin-2-ylamino]-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid 3-dimethylamino-propyl ester was prepared from 3-amino-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid 3-dimethylamino-propyl ester and 3-(2,5-Dichloro-pyrimidin-4-ylamino)-thiophene-2-carboxylic acid prop-2-ynylamide in an analogous manner to Example 1410. Product isolated as a yellow foam (116 mg, 68%). LCMS (m/e) 584 (M+H); 1H-NMR (d6-DMSO, 400 MHz) δ 11.51 (s, 1H), 9.60 (s, 1H), 8.84-8.72 (m, 1H), 8.57-8.43 (m, 1H), 8.29 (s, 1H), 7.89-7.77 (m, 1H), 7.62-7.48 (m, 1H), 7.35-7.21 (m, 1H), 7.21-7.10 (m, 1H), 4.17-3.92 (m, 7H), 3.77-3.48 (m, 2H), 3.17-3.13 (m, 1H), 2.23-2.00 (m, 7H), 2.00-1.83 (m, 2H), 1.83-1.49 (m, 2H).

Sources & evidence

ORD record: ord-2d4ecf6ece5e494db7d36061b8bdf938
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552186B2

Reaction notes

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