Sodium Bicarbonate → 2-{3-[9-Chloro-2-(3,4-dimethoxy-phenylamino)-6-oxo-5,6-dihydrobenzo[b]pyrimido[4,5-d]azepin-7-yl]-propyl}-isoindole-1,3-dione

HRID 2373435Notes

Reaction equation

C([O-])(O)=O.[Na+].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([NH:16][C:17]([NH2:19])=[NH:18])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[C:30](=O)[C:29](=[CH:32]N(C)C)[CH2:28][C:27](=[O:36])[N:26]([CH2:37][CH2:38][CH2:39][N:40]3[C:48](=[O:49])[C:47]4[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=4)[C:41]3=[O:50])[C:25]=2[CH:51]=1>>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]2[C:30]3[N:18]=[C:17]([NH:16][C:10]4[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:8]([O:7][CH3:6])[CH:9]=4)[N:19]=[CH:32][C:29]=3[CH2:28][C:27](=[O:36])[N:26]([CH2:37][CH2:38][CH2:39][N:40]3[C:41](=[O:50])[C:42]4[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=4)[C:48]3=[O:49])[C:25]=2[CH:51]=1

Participants

Reactant 3

HCID 516892Sodium Bicarbonate

HCID 669347928-Chloro-4-((dimethylamino)methylene)-1-(3-(1,3-dioxoisoindolin-2-yl)propyl)-3,4-dihydro-1H-benzo[b]azepine-2,5-dione

HCID 178492306N-(3,4-dimethoxyphenyl)guanidine

Product 1

HCID 598514412-{3-[9-Chloro-2-(3,4-dimethoxy-phenylamino)-6-oxo-5,6-dihydrobenzo[b]pyrimido[4,5-d]azepin-7-yl]-propyl}-isoindole-1,3-dione

Procedure

In a manner similar to that described for method I (NaHCO3 used instead of K2CO3), 1-(3,4-dimethoxyphenyl)guanidine and 8-chloro-4-((dimethylamino)-methylene)-1-(3-(1,3-dioxoisoindolin-2-yl)propyl)-3,4-dihydro-1H-benzo[b]azepine-2,5-dione (I-40-b) were converted to I-40-c and carried on crude: MS m/z═584 (M+H).

Sources & evidence

ORD record: ord-cb10258cdf3848d48484a757c4a2cbe3
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459448B2

Reaction notes

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