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

HRID 11112Notes

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][N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]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][N:35]3[CH2:36][CH2:37][O:38][CH2:39][CH2:40]3)=[O:31])[C:10]=2[CH:9]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 914862873-(4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)-N-[2-(4-morpholinyl)ethyl]propanamide

Product 1

HCID 100761583-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)-N-[2-(4-morpholinyl)ethyl]propanamideYield 64%

Procedure

Demethylation of (120) prepared as described in example 233 with BBr3 using the procedure described in example 80 except that the reaction time was 16 h gave (121) as a yellow powder (64%), mp 143–148° C. (dec). 1H NMR δ [(CD3)2SO] 11.05 (s, 1H), 9.35 (s, 1H), 8.36 (d, J=2.4 Hz, 1H), 7.74 (t, J=5.6 Hz, 1H), 7.71 (s, 1H), 7.60–7.55 (m, 2H), 7.52–7.43 (m, 3H), 7.13 (dd, J=8.8, 2.4 Hz, 1H), 4.67 (t, J=6.3 Hz, 2H), 3.40 (t, J=4.7 Hz, 4H), 2.98 (m, 2H), 2.57 (t, J=6.3 Hz, 2H), 2.12 (t, J=4.7 Hz, 4H), 2.02 (t, J=6.7 Hz, 1H). Found: C, 62.37; H, 4.99; N, 9.82. C29H27ClN4O5.1/2H2O requires C, 62.64; H, 5.08; N, 10.08.

Sources & evidence

ORD record: ord-7b6a5fef751a4360973346568a5ff73a
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094798B1

Reaction notes

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