2-Chloropyrimidine → HCID 11417002, compound

HRID 898336Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[CH:11]([NH2:16])[CH2:12][CH2:13][CH2:14][CH2:15][C:5]2=1.Cl[C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[CH:11]([NH:16][C:18]3[N:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:12][CH2:13][CH2:14][CH2:15][C:5]2=1

Participants

Reactant 2

HCID 744042-Chloropyrimidine

HCID 59691864HCID 59691864, compound

Product 1

HCID 11417002HCID 11417002, compound

Procedure

2-Bromo-N-pyrimidin-2-yl-5,6,7,8,9,10-hexahydrocyclohepta[b]indol-6-amine was prepared from 2-bromo-5,6,7,8,9,10-hexahydrocyclohepta[b]indol-6-amine (150 mg, 0.54 mmol) and 2-chloropyrimidine (123 mg, 1.07 mmol) in a similar manner as described in Example 22 to give 18 mg (9%) of a yellow solid. 1H-NMR (DMSO-d6): δ 10.80 (s, 1H), 8.31 (d, 2H), 7.57 (s, 1H), 7.49 (d, 1H), 7.20 (d, 1H), 7.07-7.04 (m, 1H), 6.60 (t, 1H), 5.36-533 (m, 1H), 2.94-2.89 (m, 1H), 2.70-2.63 (m, 1H), 2.05-1.94 (m, 2H), 1.89-1.59 (m, 4H); MS m/z (M+1) 357, 359; (M−1) 355, 357.

Sources & evidence

ORD record: ord-80c45a07ad244f65bc7cac815e035f16
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351733B2

Reaction notes

Loading…