Benzimidazole → HCID 59606044, compound

HRID 1945783Notes

Reaction equation

HRID 1945783 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.ClC1[N:12]=[C:13]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[C:14]2[S:19][C:18]([CH2:20][N:21]3[CH2:30][CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22]3)=[CH:17][C:15]=2[N:16]=1.NC1C=CC=CC=1N>>[CH2:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:29][CH2:30][N:21]1[CH2:20][C:18]1[S:19][C:14]2[C:13]([N:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)=[N:12][C:2]([NH:3][C:4]3[C:5]([NH2:1])=[CH:6][CH:7]=[CH:8][CH:9]=3)=[N:16][C:15]=2[CH:17]=1

Participants

4

Reactant 3

HCID 5798BenzimidazoleHCID 7243O-PhenylenediamineHCID 86624275HCID 86624275, compound

Product 1

HCID 59606044HCID 59606044, compound

Procedure

Following General Procedure J for Multi-Step Benzimidazole Formation by Buchwald coupling, 4-(2-chloro-6-((3,4-dihydroisoquinolin-2(1H)-yl)methyl)thieno[3,2-d]pyrimidin-4-yl)morpholine and 1,2-diaminobenzene were reacted to give N1-(6-((3,4-dihydroisoquinolin-2(1H)-yl)methyl)-4-morpholinothieno[3,2-d]pyrimidin-2-yl)benzene-1,2-diamine which was cyclized with acetic acid to give 204. LCMS m/z: 497.6 (MH+)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-b616ae624e0a49b8be2ccc58fe746a13
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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