Chlorosuccinimide → HCID 69520162, compound

HRID 1944586Notes

Reaction equation

HRID 1944586 reaction equation
[NH2:1][C@:2]([C:11]1[O:15][C:14]([C:16]2[CH:21]=[C:20]([NH:22][CH2:23][C@H:24]3[CH2:26][C@@H:25]3[CH3:27])[N:19]=[C:18]([N:28]([CH3:33])[S:29]([CH3:32])(=[O:31])=[O:30])[CH:17]=2)=[N:13][CH:12]=1)([CH3:10])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1C(=O)N([Cl:41])C(=O)C1>C(Cl)Cl>[NH2:1][C@:2]([C:11]1[O:15][C:14]([C:16]2[CH:21]=[C:20]([NH:22][CH2:23][C@H:24]3[CH2:26][C@@H:25]3[CH3:27])[N:19]=[C:18]([N:28]([CH3:33])[S:29]([CH3:32])(=[O:30])=[O:31])[C:17]=2[Cl:41])=[N:13][CH:12]=1)([CH3:10])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 31398Chlorosuccinimide2×HCID 69521098HCID 69521098, compound

Product 1

HCID 69520162HCID 69520162, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

To a solution of N-[4-{5-[(1R)-1-amino-1-methyl-2-phenylethyl]-1,3-oxazol-2-yl}-6-({[(1S,25)-2-methylcyclopropyl]methyl}amino)pyridin-2-yl]-N-methylmethanesulfonamide (0.009 g, 0.015 mmol) in 0.3 mL CH2Cl2 was added 0.09 mL of a 0.15M stock solution of NCS in CH2Cl2. After 15 h, a further 0.10 mL CH2Cl2 and 0.1 mL 0.15 M stock solution of NCS in CH2Cl2 were added. After 24 h, the reaction was concentrated, redissolved in DMF and purified by preparative HPLC to afford N-[4-{5-[(1R)-1-amino-1-methyl-2-phenylethyl]-1,3-oxazol-2-yl}-3-chloro-6-({[(1S,2S)-2-methylcyclopropyl]methyl}amino)pyridin-2-yl]-N-methylmethanesulfonamide as a yellow solid. 1H NMR (400 MHz, d4-MeOH) δ 7.30-7.29 (m, 3H), 7.24 (s, 1H), 7.04-7.02 (m, 3H), 3.47 (d, J=13.3 Hz, 1H), 3.28 (s, 3H), 3.26-3.20 (m, 5H), 1.71 (s, 3H), 1.06 (d, J=5.9 Hz, 3H), 0.85 (m, 1H), 0.71 (m, 1H), 0.43 (m, 1H), 0.27 (m, 1H). LCMS (M+H)=505 (chlorine pattern).

Workup

  1. waitAfter 24 h
  2. concentrationthe reaction was concentrated
  3. dissolutionredissolved in DMF
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-2740ae1158d844fbb9d3920eb2633fbc
Source dataset
uspto-grants-2013_03
Patent number
US08394837B2

Reaction notes

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