Hydrochloric Acid → HCID 86689959, compound

HRID 716852Notes

Reaction equation

HRID 716852 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH2:30][CH2:31][Cl:32])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:29])[NH:13][C:14]2[CH:15]=[C:16]([NH:20][C:21](=[O:28])[CH2:22][N:23]3[CH2:27]CC[CH2:24]3)[CH:17]=[CH:18][CH:19]=2)=[CH:7][CH:6]=1.Cl.ClCCN(CCCl)C1C=CC(NC(=O)NC2C=C(NC(=O)CCl)C=CC=2)=CC=1.N1CCCC1>C1COCC1>[ClH:1].[Cl:1][CH2:2][CH2:3][N:4]([CH2:30][CH2:31][Cl:32])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:29])[NH:13][C:14]2[CH:15]=[C:16]([NH:20][C:21](=[O:28])[CH2:22][N:23]([CH3:27])[CH3:24])[CH:17]=[CH:18][CH:19]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 86689957HCID 86689957, compoundHCID 86689960HCID 86689960, compound

Product 1

HCID 86689959HCID 86689959, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By following the same procedure as that for BO-2189, N-(3-(3-(4-(bis(2-chloroethyl)amino)phenyl)ureido)-phenyl)-2-(pyrrolidin-1-yl)acetamide (BO-2151) hydrochloride was prepared from N-(3-(3-(4-(bis(2-chloroethyl)amino)phenyl)ureido)phenyl)-2-chloroacetamide (2.2 g, 5.0 mmol) and pyrrolidine (1.6 g, 20 mmol) in THF (50 mL), 1.6 g (69%), mp 66-68° C. 1H NMR (DMSO-d6) δ: 1.90-1.93 (2H, m, CH2), 1.98-2.01 (2H, m, CH2), 3.11-3.15 (2H, m, CH2), 3.61-3.64 (2H, m, CH2), 3.66-3.72 (8H, m, CH2), 6.72-6.74 (2H, d, J=7.8 Hz, Ar—H), 7.19-7.22 (2H, d, J=7.6 Hz, Ar—H), 7.29-7.32 (3H, m, Ar—H), 7.78 (1H, s, Ar—H), 9.04 (1H, brs, NH), 9.31 (1H, brs, NH), 10.35 (1H, brs, NH). 13C NMR (CDCl3, 125 MHz) δ: 22.82, 41.05, 52.88, 54.04, 55.72, 108.81, 112.53, 113.50, 120.03, 129.05, 138.43, 140.72, 152.87, 163.35. HRMS [ES+]: calcd for C23H29Cl2N5O2, 478.4147 [M+H]+. found 478.1777. HPLC 98.6%.

Sources & evidence

ORD record
ord-dd4c88b245c24abf89acdb1884874086
Source dataset
uspto-grants-2015_11
Patent number
US09193687B2

Reaction notes

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