4-Methylmorpholine → HCID 45109856, compound

HRID 2359013Notes

Reaction equation

HRID 2359013 reaction equation
Cl.[O:2]=[C:3]1[CH2:8][NH:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][N:4]1[C:15]1([C:18]([OH:20])=O)[CH2:17][CH2:16]1.[NH2:21][C:22]1[CH:23]=[C:24]2[CH2:40][C:29]3([O:34][C:33]4[CH:35]=[CH:36][CH:37]=[N:38][C:32]=4[NH:31][C:30]3=[S:39])[CH2:28][C:25]2=[N:26][CH:27]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[O:2]=[C:3]1[CH2:8][NH:7][CH:6]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:5][N:4]1[C:15]1([C:18]([NH:21][C:22]2[CH:23]=[C:24]3[CH2:40][C:29]4([O:34][C:33]5[CH:35]=[CH:36][CH:37]=[N:38][C:32]=5[NH:31][C:30]4=[S:39])[CH2:28][C:25]3=[N:26][CH:27]=2)=[O:20])[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58431970HCID 58431970, compound2×HCID 67299934HCID 67299934, compound

Product 1

HCID 45109856HCID 45109856, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2-oxo-5-phenylpiperazin-1-yl)cyclopropanecarboxylic acid hydrochloride (57 mg, 0.22 mmol) [Wood et al. US 2007/0265225], 3-amino-5,7-dihydrospiro[cyclopenta[b]pyridine-6,2′-pyrido[3,2-b][1,4]oxazine]-3′(4′H)-thione (Intermediate 1, 57 mg, 0.20 mmol) and HATU (84 mg, 0.22 mmol) in DMF (2 mL) is treated with N-methylmorpholine (0.096 mL, 0.88 mmol). The mixture is stirred at rt for 18 h and is then purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. The pure, product-containing fractions are combined and lyophilized to afford the title compound.

Workup

  1. customis then purified directly by HPLC
  2. washeluting with a gradient of H2O
  3. additionThe pure, product-containing fractions

Sources & evidence

ORD record
ord-84e6b0ffabca4fe19bbf0f98d1308366
Source dataset
uspto-grants-2014_04
Patent number
US08685965B2

Reaction notes

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