Morpholine → HCID 10885591, compound

HRID 1835097Notes

Reaction equation

HRID 1835097 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[N:11]([CH3:29])[C:12]2[C:21]3[C:20](=[O:22])[NH:19][C:18]([CH3:23])=[C:17]([CH2:24][C:25](O)=[O:26])[C:16]=3[CH:15]=[CH:14][C:13]=2[N:28]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[NH:52]1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1>CN(C=O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:9][C:10]1[N:11]([CH3:29])[C:12]2[C:21]3[C:20](=[O:22])[NH:19][C:18]([CH3:23])=[C:17]([CH2:24][C:25]([N:52]4[CH2:57][CH2:56][O:55][CH2:54][CH2:53]4)=[O:26])[C:16]=3[CH:15]=[CH:14][C:13]=2[N:28]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11070040HCID 11070040, compound

Product 1

HCID 10885591HCID 10885591, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2,6-dichlorophenylamino)-1,7-dimethyl-9-oxo-1,8-dihydro-imidazo[4,5-h]isoquinolin-6-yl acetic acid (prepared using Methods C and A) (1.0 g, 2.3 mmol) in DMF (7 mL) was added O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) (0.82 g, 2.6 mmol) and morpholine (0.24 mL, 2.8 mmol), and the mixture stirred 18 h at room temperature. Ice water was added, the precipitate collected, washed with water and dried to give the title compound, 0.97 g, 84%, mp >300° C.; MS (ES) 500, 502 (MH+).

Workup

  1. customthe precipitate collected
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-0f4e02291b9b44f29227f8db8064fff1
Source dataset
uspto-grants-2004_08
Patent number
US06770639B2

Reaction notes

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