1-(Prop-2-yn-1-yl)pyrrolidine → 9-Chloro-2-[3-(3-pyrrolidin-1-yl-prop-1-ynyl)-phenylamino]-5H,7H-benzo[b]-pyrimido[4,5-d]azepin-6one

HRID 2373417Notes

Reaction equation

HRID 2373417 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[N:12]=[C:13]([NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19](I)[CH:18]=4)[N:14]=[CH:15][C:10]=3[CH2:9][C:8](=[O:24])[NH:7][C:6]=2[CH:25]=1.[CH2:26]([N:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1)[C:27]#[CH:28]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[N:12]=[C:13]([NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:28]#[C:27][CH2:26][N:29]5[CH2:33][CH2:32][CH2:31][CH2:30]5)[CH:18]=4)[N:14]=[CH:15][C:10]=3[CH2:9][C:8](=[O:24])[NH:7][C:6]=2[CH:25]=1

Participants

3

Reactant 2

HCID 2996161-(Prop-2-yn-1-yl)pyrrolidineHCID 598512839-Chloro-2-(3-iodo-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

Product 1

HCID 598516319-Chloro-2-[3-(3-pyrrolidin-1-yl-prop-1-ynyl)-phenylamino]-5H,7H-benzo[b]-pyrimido[4,5-d]azepin-6one

Procedure

In a manner similar to that described for Method O, 9-chloro-2-(3-iodo-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one (v-j) and 1-(prop-2-ynyl)pyrrolidine were converted to I-89 (46%): MS (AA) Rt═1.32 min, m/z═444 (M+H).

Sources & evidence

ORD record
ord-1144ae30c9b94678af4bb8df63f579ee
Source dataset
uspto-grants-2008_12
Patent number
US07459448B2

Reaction notes

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