Propargyl alcohol → 9-Chloro-2-[4-(3-hydroxy-prop-1-ynyl)-phenylamino]-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

HRID 2373409Notes

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][C:20](I)=[CH:19][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]([OH:29])[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][C:20]([C:28]#[C:27][CH2:26][OH:29])=[CH:19][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

Reactant 2

HCID 7859Propargyl alcohol

HCID 569465889-Chloro-2-(4-iodo-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

Product 1

HCID 598514029-Chloro-2-[4-(3-hydroxy-prop-1-ynyl)-phenylamino]-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one

Procedure

In a manner similar to that described for Method O, 9-chloro-2-(4-iodo-phenylamino)-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one (I-36) and prop-2-yn-1-ol were converted to I-54 (86%): HRMS Calcd. for C21H15ClN4O2: 391.0961, Found 391.0960.

Sources & evidence

ORD record: ord-346ab62cfb32434f8ac2bc911d7574d4
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459448B2

Reaction notes

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