1-(Prop-2-yn-1-yl)pyrrolidine → 2-(3,4-Dimethoxy-phenylamino)-10-(3-pyrrolidin-1-yl-prop-1-ynyl)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

HRID 2373430Notes

Reaction equation

HRID 2373430 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[N:13]=[CH:14][C:15]3[CH2:21][C:20](=[O:22])[NH:19][C:18]4[CH:23]=[CH:24][C:25](I)=[CH:26][C:17]=4[C:16]=3[N:28]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:29]([N:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1)[C:30]#[CH:31]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[N:13]=[CH:14][C:15]3[CH2:21][C:20](=[O:22])[NH:19][C:18]4[CH:23]=[CH:24][C:25]([C:31]#[C:30][CH2:29][N:32]5[CH2:36][CH2:35][CH2:34][CH2:33]5)=[CH:26][C:17]=4[C:16]=3[N:28]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 2996161-(Prop-2-yn-1-yl)pyrrolidineHCID 598511522-(3,4-Dimethoxy-phenylamino)-10-iodo-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

Product 1

HCID 598513132-(3,4-Dimethoxy-phenylamino)-10-(3-pyrrolidin-1-yl-prop-1-ynyl)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

Procedure

In a manner similar to Method O, 2-(3,4-dimethoxy-phenylamino)-10-iodo-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one (I-26) and 1-(prop-2-ynyl)pyrrolidine were converted to I-31 (29%): HRMS Calcd. for C27H27N5O3: 470.2192, Found 470.2185.

Sources & evidence

ORD record
ord-8c915f9bdd0346dca8c52fdc6e677192
Source dataset
uspto-grants-2008_12
Patent number
US07459448B2

Reaction notes

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