1,2-Dichloroethane → HCID 86636991, compound

HRID 1366582Notes

Reaction equation

HRID 1366582 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:11][N:12]([CH:20]=[O:21])[O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:22][C:23]1[N:28]=[C:27]([NH:29][NH2:30])[C:26]([F:31])=[C:25]([N:32]2[CH2:35][C:34]([CH3:41])([N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[CH2:33]2)[N:24]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C>[Cl:22][C:23]1[N:28]=[C:27]([NH:29][NH:30][C:8](=[O:10])[C@H:7]([CH2:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH2:11][N:12]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH:20]=[O:21])[C:26]([F:31])=[C:25]([N:32]2[CH2:33][C:34]([CH3:41])([N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[CH2:35]2)[N:24]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 57937086(2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoic acidHCID 86636992HCID 86636992, compound

Product 1

HCID 86636991HCID 86636991, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoic acid (112 mg, 0.374 mmol), 2-chloro-5-fluoro-4-hydrazino-6-[3-methyl-3-(1-pyrrolidinyl)-1-azetidinyl]pyrimidine (assumed 112 mg of free base, 0.374 mmol), EDC (86 mg, 0.449 mmol), HOAt (56 mg, 0.411 mmol), and NMM (0.25 mL, 2.24 mmol) in DMF (5 ml) was stirred at room temperature overnight. The reaction mixture was then purified via 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](tetrahydro-2H-pyran-2-yloxy)formamide (145 mg, 66%). LCMS: (M+H)+: 582.5.

Workup

  1. customThe reaction mixture was then purified via RP-HPLC

Sources & evidence

ORD record
ord-1d710dfd9b4f419784ae441d55d4591d
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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