Boron tribromide → 3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1H)-yl)-N-[2-(1H-imidazol-5-yl)ethyl]propanamide

HRID 11118Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([O:26]C)[CH:14]=[CH:13][C:12]=3[N:11]([CH2:28][CH2:29][C:30]([NH:32][CH2:33][CH2:34][C:35]3[NH:39][CH:38]=[N:37][CH:36]=3)=[O:31])[C:10]=2[CH:9]=1.B(Br)(Br)Br>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([OH:26])[CH:14]=[CH:13][C:12]=3[N:11]([CH2:28][CH2:29][C:30]([NH:32][CH2:33][CH2:34][C:35]3[NH:39][CH:38]=[N:37][CH:36]=3)=[O:31])[C:10]=2[CH:9]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 867602123-(4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)-N-[2-(1H-imidazol-5-yl)ethyl]propanamide

Product 1

HCID 104369463-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1H)-yl)-N-[2-(1H-imidazol-5-yl)ethyl]propanamideYield 46%

Procedure

Demethylation of (128) prepared as described in example 241 with BBr3 using the procedure described in example 80 except that the reaction time was 48 h gave (129) as a yellow powder (46%), mp 158–162° C. (dec). 1H NMR δ [(CD3)2SO] 11.75 (br, 1H), 11.05 (br s, 1H), 9.36 (br s, 1H), 8.37 (d, J=2.4 Hz, 1H), 7.91 (t, J=5.3 Hz, 1H), 7.71 (s, 1H), 7.59–7.54 (m, 2H), 7.50–7.42 (m, 4H), 7.14 (dd, J=8.8, 2.4 Hz, 1H), 6.57 (br, 1H), 4.65 (t, J=6.5 Hz, 2H), 3.13 (m, 2H), 2.55 (t, J=6.5 Hz, 1H), 2.40 (t, J=6.5 Hz, 1H). FABMS found [M+H]+: 530.1431, 528.1440. C28H23ClN5O4 requires 530.1409, 528.1439.

Sources & evidence

ORD record: ord-2b59472ebce341ce8560e7ca3d38bb3e
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094798B1

Reaction notes

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