HCID 67263949, compound → HCID 66829725, compound

HRID 1041478Notes

Reaction equation

NC1C=CC2C(=O)NCCN(CC)C=2C=1.OC(C(F)(F)F)=O.[Cl:23][C:24]1[C:25]([NH:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[O:52][CH2:53][CH2:54][N:55]2[CH2:60][CH2:59][O:58][CH2:57][CH2:56]2)=[N:26][C:27]([NH:30][C:31]2[CH:32]=[CH:33][C:34]3[C:40](=[O:41])[NH:39][CH2:38][CH2:37][N:36]([CH2:42][CH3:43])[C:35]=3[CH:44]=2)=[N:28][CH:29]=1>>[Cl:23][C:24]1[C:25]([NH:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[O:52][CH2:53][CH2:54][N:55]2[CH2:60][CH2:59][O:58][CH2:57][CH2:56]2)=[N:26][C:27]([NH:30][C:31]2[CH:32]=[CH:33][C:34]3[C:40](=[O:41])[NH:39][CH2:38][CH2:37][N:36]([CH2:42][CH3:43])[C:35]=3[CH:44]=2)=[N:28][CH:29]=1

Participants

Reactant 2

HCID 67263949HCID 67263949, compound

HCID 86667316HCID 86667316, compound

Product 1

HCID 66829725HCID 66829725, compound

Procedure

Following an analogous procedure as described in Example 1451, 8-amino-1-ethyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one was converted to 8-{5-Chloro-4-[2-(2-morpholin-4-yl-ethoxy)-phenylamino]-pyrimidin-2-ylamino}-1-ethyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one TFA salt (78 mg, 56%). 1H-NMR (DMSO-D6, 400 MHz) 6 NMR 9.50 (bs, 1H), 9.40 (s, 1H), 8.45 (s, 1H), 8.16 (s, 1H), 7.87 (d, 1H), 7.38 (d, 1H), 7.30 (t, 1H), 7.20 9d, 1H), 6.85 (t, 1H), 6.80 (bs, 2H), 4.42 (s, 2H), 3.94 (t, 2H), 3.35-3.70 (m, 12H), 3.0-3.25 (m, 2H), 1.07 (t, 3H). LC/MS (ESI+) 558.37 (M+H). MP 223-225° C.

Sources & evidence

ORD record: ord-6b3ec7ffcc984501a5988b9ef69f0b74
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552186B2

Reaction notes

Loading…