1,2-Dichloroethane → HCID 86637025, compound

HRID 1366663Notes

Reaction equation

HRID 1366663 reaction equation
Cl.Cl.Cl.[NH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][N:11]([CH3:22])[C:12]2[NH:17][C:16]([Cl:18])=[N:15][C:14](=[N:19][NH2:20])[C:13]=2[F:21])[N:9]=1.[CH:23]1([CH2:28][C@H:29]([CH2:33][N:34]([CH:42]=[O:43])[O:35][CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][O:37]2)[C:30](O)=[O:31])[CH2:27][CH2:26][CH2:25][CH2:24]1.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>CN(C=O)C>[NH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][N:11]([CH3:22])[C:12]2[N:17]=[C:16]([Cl:18])[N:15]=[C:14]([NH:19][NH:20][C:30](=[O:31])[C@H:29]([CH2:28][CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[CH2:33][N:34]([O:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][O:37]3)[CH:42]=[O:43])[C:13]=2[F:21])[N:9]=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 178483003HCID 178483003, compound

Product 1

HCID 86637025HCID 86637025, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-[[(2-Amino-1,3-thiazol-4-yl)methyl](methyl)amino]-2-chloro-5-fluoro-4(1H)-pyrimidinone hydrazone trihydrochloride (150 mg, 0.29 mmol), (2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoic acid (120 mg, 0.4 mmol), and HOAt (59 mg, 0.43 mmol) were dissolved in 10 mL of DMF. NMM (0.2 mL, 1.8 mmol) was added, followed by EDC (85 mg, 0.43 mmol). After stirring overnight at room temperature, the reaction mixture was purified by RP-HPLC [(2R)-3-(2-{6-[[(2-amino-1,3-thiazol-4-yl)methyl](methyl)amino]-2-chloro-5-fluoro-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide (110 mg, 52%). LCMS: (M+H)+: 585.2.

Workup

  1. customthe reaction mixture was purified by RP-HPLC [(2R)-3-(2-{6-[[(2-amino-1,3-thiazol-4-yl)methyl](methyl)amino]-2-chloro-5-fluoro-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide (110 mg, 52%)

Sources & evidence

ORD record
ord-a9a8d5a0067f4a7eb2f5cfc7d2014952
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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