1,2-Dichloroethane → HCID 86637010, compound

HRID 1366628Notes

Reaction equation

HRID 1366628 reaction equation
Cl.Cl.[Cl:3][C:4]1[NH:5][C:6]([NH:13][CH2:14][C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)=[C:7]([F:12])[C:8](=[N:10][NH2:11])[N:9]=1.C(NC(C)C)(C)C.[CH:27]1([CH2:32][C@H:33]([CH2:37][N:38]([CH:46]=[O:47])[O:39][CH:40]2[CH2:45][CH2:44][CH2:43][CH2:42][O:41]2)[C:34](O)=[O:35])[CH2:31][CH2:30][CH2:29][CH2:28]1.CN1CCOCC1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[Cl:3][C:4]1[N:9]=[C:8]([NH:10][NH:11][C:34](=[O:35])[C@H:33]([CH2:32][CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31]2)[CH2:37][N:38]([O:39][CH:40]2[CH2:45][CH2:44][CH2:43][CH2:42][O:41]2)[CH:46]=[O:47])[C:7]([F:12])=[C:6]([NH:13][CH2:14][C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)[N:5]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 86637011HCID 86637011, compoundHCID 178478859HCID 178478859, compound

Product 1

HCID 86637010HCID 86637010, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-5-fluoro-6-[(3-thienylmethyl)amino]-4(1H)-pyrimidinone hydrazone dihydrochloride (1.0828 g) and (2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoic acid diisopropyl amine salt form (1.63 g, 3.8 mmol) were dissolved in DMF (9 mL). NMM (2.1 mL, 19.1 mmol) was added, followed by HOAt (0.512 g, 3.76 mmol) and EDC (0.722 g, 3.77 mmol). After stirring overnight, the reaction mixture was purified by RP-HPLC to provide [(2R)-3-(2-{2-chloro-5-fluoro-6-[(3-thienylmethyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide as a reddish brown solid (0.7045 g). LCMS: (M+H−THP)+=471.1.

Workup

  1. customthe reaction mixture was purified by RP-HPLC

Sources & evidence

ORD record
ord-61d116011fb343b288c30ae41f439057
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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