Chlorosuccinimide → HCID 69073101, compound

HRID 1987168Notes

Reaction equation

HRID 1987168 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C@@H:9]([CH2:45][F:46])[C@@H:10]([NH:18][C:19](=[O:44])[C:20]1[CH:25]=[C:24]([N:26]([CH2:32][CH2:33][O:34][CH3:35])[CH2:27][C@H:28]2[CH2:30][C@@H:29]2[CH3:31])[N:23]=[C:22]([N:36]([S:38]([CH:41]([CH3:43])[CH3:42])(=[O:40])=[O:39])[CH3:37])[CH:21]=1)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1C(=O)N(Cl)C(=O)C1>C(Cl)Cl>[NH2:8][C@@H:9]([CH2:45][F:46])[C@@H:10]([NH:18][C:19](=[O:44])[C:20]1[CH:25]=[C:24]([N:26]([CH2:32][CH2:33][O:34][CH3:35])[CH2:27][C@H:28]2[CH2:30][C@@H:29]2[CH3:31])[N:23]=[C:22]([N:36]([S:38]([CH:41]([CH3:43])[CH3:42])(=[O:39])=[O:40])[CH3:37])[CH:21]=1)[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 69073100HCID 69073100, compound

Product 1

HCID 69073101HCID 69073101, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[(1S,2R)-2-amino-1-benzyl-3-fluoropropyl]-2-[(isopropylsulfonyl)(methyl)amino]-6-((2-methoxyethyl){[(1S,2S)-2-methylcyclopropyl]methyl}amino)isonicotinamide was prepared via procedure described in Example 95. A solution of N-[(1S,2R)-2-amino-1-benzyl-3-fluoropropyl]-2-[(isopropylsulfonyl)(methyl)amino]-6-((2-methoxyethyl){[(1S,2S)-2-methylcyclopropyl]methyl}amino)isonicotinamide trifluoroacetate (0.11 g, 0.2 mmol) in 5 mL methylene chloride was treated with NCS (0.026 g, 0.2 mmol) and the resulting mixture was stirred at ambient temperature for 24 hours. The reaction was evaporated in vacuo and purified by reverse phase LC to generate N-[(1S,2R)-2-amino-1-benzyl-3-fluoropropyl]-3-chloro-2-[(isopropylsulfonyl)(methyl)amino]-6-((2-methoxyethyl){[(1S,2S)-2-methylcyclopropyl]methyl}amino)isonicotinamide trifluoroacetate as a yellow solid: 1H NMR (CDCl3) δ 7.25 (m, 5H), 6.21 (s, 1H), 4.65 (m, 4H), 3.85 (m, 1H), 3.60 (m, 3H), 3.40 (m, 3H), 3.31 (s, 3H), 3.22 (s, 3H), 3.18 (m, 2H), 1.42 (m, 6H), 1.01 (d, J=5.8 Hz, 3H), 0.64 (m, 2H), 0.36 (m, 1H), 0.25 (m, 1H). ES MS (M+H)=598.8.

Workup

  1. customThe reaction was evaporated in vacuo
  2. custompurified by reverse phase LC

Sources & evidence

ORD record
ord-73f263f0d6d94a958389dd1e34adb0cf
Source dataset
uspto-grants-2009_06
Patent number
US07550481B2

Reaction notes

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