1,2-Dichloroethane → ((2R)-2-(cyclopentylmethyl)-3-{2-[6-(2,5-dihydro-1H-pyrrol-1-yl)-5-fluoro-2-methyl-4-pyrimidinyl]hydrazino}-3-oxopropyl)(tetrahydro-2H-pyran-2-yloxy)formamide

HRID 1366401Notes

Reaction equation

HRID 1366401 reaction equation
[N:1]1([C:6]2[C:11]([F:12])=[C:10]([NH:13][NH2:14])[N:9]=[C:8]([CH3:15])[N:7]=2)[CH2:5][CH:4]=[CH:3][CH2:2]1.[CH:16]1([CH2:21][C@H:22]([CH2:26][N:27]([CH:35]=[O:36])[O:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][O:30]2)[C:23](O)=[O:24])[CH2:20][CH2:19][CH2:18][CH2:17]1.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>CN(C=O)C>[CH:16]1([CH2:21][C@@H:22]([C:23]([NH:14][NH:13][C:10]2[C:11]([F:12])=[C:6]([N:1]3[CH2:2][CH:3]=[CH:4][CH2:5]3)[N:7]=[C:8]([CH3:15])[N:9]=2)=[O:24])[CH2:26][N:27]([O:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][O:30]2)[CH:35]=[O:36])[CH2:20][CH2:19][CH2:18][CH2:17]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 669361874-(2,5-dihydro-1H-pyrrol-1-yl)-5-fluoro-6-hydrazino-2-methylpyrimidine

Product 1

HCID 86636924((2R)-2-(cyclopentylmethyl)-3-{2-[6-(2,5-dihydro-1H-pyrrol-1-yl)-5-fluoro-2-methyl-4-pyrimidinyl]hydrazino}-3-oxopropyl)(tetrahydro-2H-pyran-2-yloxy)formamideYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(2,5-Dihydro-1H-pyrrol-1-yl)-5-fluoro-6-hydrazino-2-methylpyrimidine (142 mg, 0.68 mmol), (2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoic acid (242 mg, 0.81 mmol), and HOAt (110 mg, 0.81 mmol) were dissolved in 4 mL of DMF. NMM (370 μL, 3.4 mmol) was added, followed by EDC (155 mg, 0.81 mmol). When the starting materials were consumed, the reaction mixture was purified by RP-HPLC to provide ((2R)-2-(cyclopentylmethyl)-3-{2-[6-(2,5-dihydro-1H-pyrrol-1-yl)-5-fluoro-2-methyl-4-pyrimidinyl]hydrazino}-3-oxopropyl)(tetrahydro-2H-pyran-2-yloxy)formamide (140 mg, 55%).

Workup

  1. customWhen the starting materials were consumed
  2. customthe reaction mixture was purified by RP-HPLC

Sources & evidence

ORD record
ord-206c4dd841724b8791741696367d8d12
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

Loading…