Acetic Acid → HCID 58000601, compound

HRID 1366583Notes

Reaction equation

HRID 1366583 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][NH:9][C:10](=[O:29])[C@H:11]([CH2:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:12][N:13]([O:16]C2CCCCO2)[CH:14]=[O:15])[C:5]([F:30])=[C:4]([N:31]2[CH2:34][C:33]([CH3:40])([N:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)[CH2:32]2)[N:3]=1.CC(O)=O>O>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][NH:9][C:10](=[O:29])[C@H:11]([CH2:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:12][N:13]([OH:16])[CH:14]=[O:15])[C:5]([F:30])=[C:4]([N:31]2[CH2:32][C:33]([CH3:40])([N:35]3[CH2:36][CH2:37][CH2:38][CH2:39]3)[CH2:34]2)[N:3]=1

Participants

4

Reactant 2

HCID 176Acetic Acid2×HCID 86636991HCID 86636991, compound

Product 1

HCID 58000601HCID 58000601, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of [(2R)-3-(2-{2-chloro-5-fluoro-6-[3-methyl-3-(1-pyrrolidinyl)-1-azetidinyl]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide (145 mg) in 4:1 AcOH:water (20 mL) was stirred at room temperature overnight. LCMS indicated ˜45% completion of the deprotection. Another portion of the mixed solvents (4:1 AcOH:water, 20 mL) was added, and stirring continued overnight. The solvents were then removed in vacuo, and the resulting crude product was purified by RP-HPLC to provide [(2R)-3-(2-{2-chloro-5-fluoro-6-[3-methyl-3-(1-pyrrolidinyl)-1-azetidinyl]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide (45 mg, 36%). LCMS: (M+H)+: 498.2.

Workup

  1. customThe solvents were then removed in vacuo
  2. customthe resulting crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-70fa722e1d7241bea009a476208a24a2
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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