Dimethylformamide → HCID 86689961, compound

HRID 716853Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:18])[CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:5]=[CH:6][CH:7]=1.Cl.[Cl:20][CH2:21][CH2:22][N:23]([CH2:31][CH2:32][Cl:33])[C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1.CN([CH:37]=[O:38])C>>[Cl:20][CH2:21][CH2:22][N:23]([CH2:31][CH2:32][Cl:33])[C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:37](=[O:38])[NH:1][C:2]2[CH:3]=[C:4]([NH:8][C:9](=[O:18])[CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[CH:5]=[CH:6][CH:7]=2)=[CH:26][CH:25]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 2157271,4-Benzenediamine, N1,N1-bis(2-chloroethyl)-, hydrochloride (1:?)

HCID 16782927HCID 16782927, compound

Product 1

HCID 86689961HCID 86689961, compound

Procedure

By following the same procedure as that for BO-2091, BO-2147 was prepared from N-(3-aminophenyl)-3-(piperidin-1-yl)propanamide (2.47 g, 10.0 mmol) and N-mustard isocyanate [19, freshly prepared from N-mustard amine hydrochloride 18 (6.1 g, 20 mmol)] in dry DMF. Yield: 4.2 g (82%); mp 108-110° C. The HCl salt of compound BO-2147 was prepared by following the same procedure as that for compound BO-2091. 1H NMR (DMSO-d6) δ: 1.33-1.42 (1H, m, CH), 1.67-1.79 (5H, m, CH), 2.90-2.94 (4H, m, CH2), 3.30-3.33 (2H, m, CH2), 3.38-3.42 (2H, m, CH2), 3.69-3.74 (8H, m, CH2), 6.73-6.75 (2H, m, Ar—H), 7.16-7.18 (2H, m, Ar—H), 7.26-7.27 (3H, m, Ar—H), 7.72 (1H, s, Ar—H), 8.95 (1H, brs, NH), 9.14 (1H, brs, NH), 10.33 (1H, brs, NH). 13C NMR (CDCl3, 125 MHz) δ: 21.32, 22.37, 30.53, 40.89, 51.79, 52.13, 53.14, 108.79, 112.57, 113.03, 113.97, 119.99, 128.88, 139.31, 140.50, 152.87, 167.79. HRMS [ES+]: calcd for C25H33Cl2N5O2, 506.4678 [M+H]+. found 506.2090. HPLC 98.8%.

Sources & evidence

ORD record: ord-d90a34f44c8f49898db6fad7dd2058f6
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193687B2

Reaction notes

Loading…