4-Methylmorpholine → HCID 25174433, compound

HRID 549452Notes

Reaction equation

HRID 549452 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([OH:15])=O)=[CH:7]2)([O-:3])=[O:2].[NH2:16][C@H:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26]#[N:27])[CH:24]=2)[CH2:19][C:18]1([CH3:29])[CH3:28].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:26]([C:23]1[CH:24]=[C:25]2[C:20]([CH2:19][C:18]([CH3:29])([CH3:28])[C@H:17]2[NH:16][C:13]([C:8]2[NH:9][C:10]3[C:6]([CH:7]=2)=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=3)=[O:15])=[CH:21][CH:22]=1)#[N:27]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 3512915-Nitroindole-2-carboxylic acidHCID 516892Sodium BicarbonateHCID 67081572HCID 67081572, compound

Product 1

HCID 25174433HCID 25174433, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-nitro-1H-indole-2-carboxylic acid (144 mg, 0.698 mmol), (R)-3-amino-2,2-dimethyl-2,3-dihydro-1H-indene-5-carbonitrile (110 mg, 0.591 mmol), BOP reagent (401 mg, 0.907 mmol), N-methylmorpholine (0.30 mL, 2.73 mmol) in DMF (2 mL) was stirred at rt for 16 hr. To the mixture was added 5% NaHCO3 solution (35 mL) and the resulting mixture was stirred at rt for 15 min. The precipitating title product (250 mg) was collected as a beige solid by suction filtration and dried over Drierite® under vacuum. LCMS (M+H)+=375.25. 1H NMR (500 MHz, DMSO-d6) δ: 8.84 (d, J=9.3 Hz, 1H), 8.69 (s, 1H), 8.07 (d, J=8.8 Hz, 1H), 7.70 (d, J=8.2 Hz, 1H), 7.66 (s, 1H), 7.59 (d, J=11.0 Hz, 1H), 7.58 (s, 1H), 7.46 (d, J=7.7 Hz, 1H), 5.39 (d, J=9.3 Hz, 1H), 2.87 (dd, J=20.9, 16.5 Hz, 2H), 1.22 (s, 3H), 0.95 (s, 3H).

Workup

  1. stirringthe resulting mixture was stirred at rt for 15 min
  2. filtrationThe precipitating title product (250 mg) was collected as a beige solid by suction filtration
  3. dry with materialdried over Drierite® under vacuum

Sources & evidence

ORD record
ord-52527088c3664f00a57ee489260f5660
Source dataset
uspto-grants-2011_05
Patent number
US07943658B2

Reaction notes

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