Dimethylformamide → HCID 66661985, compound

HRID 557967Notes

Reaction equation

HRID 557967 reaction equation
Cl.[CH3:2][C:3]1([CH3:13])[C:7]2([CH2:11][CH2:10][NH:9][CH2:8]2)[O:6][C:5](=[O:12])[CH2:4]1.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3([C:36](O)=[O:37])[CH2:35][CH2:34]3)=[C:29]([F:39])[CH:28]=2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].CN(C)C=O.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>>[CH3:2][C:3]1([CH3:13])[C:7]2([CH2:11][CH2:10][N:9]([C:36]([C:33]3([C:30]4[CH:31]=[CH:32][C:27]([N:24]5[CH2:23][CH2:22][N:21]([C:19]([O:18][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:20])[CH2:26][CH2:25]5)=[CH:28][C:29]=4[F:39])[CH2:34][CH2:35]3)=[O:37])[CH2:8]2)[O:6][C:5](=[O:12])[CH2:4]1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66661939HCID 66661939, compoundHCID 66662352HCID 66662352, compound

Product 1

HCID 66661985HCID 66661985, compound

Procedure

To a mixture of 4,4-dimethyl-1-oxa-7-azaspiro[4.4]nonan-2-one hydrochloride (20.3 mg, 0.0000988 mol) and 1-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-2-fluorophenyl}cyclopropanecarboxylic acid (36.0 mg, 0.0000988 mol) in N,N-dimethylformamide (0.30 mL, 0.0039 mol) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (48.1 mg, 0.000109 mol) followed by N,N-diisopropylethylamine (0.0206 mL, 0.000118 mol). After stirring at rt for 1 h, the reaction mixture was quenched with water and extracted with EtOAc. The organic layers were combined, washed with brine, and dried. The crude residue was used directly in the next step without further purification. LCMS (M+H) 516.3. (M+Na) 538.3.

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. customdried
  5. customThe crude residue was used directly in the next step without further purification

Sources & evidence

ORD record
ord-b16796024de242e48c8f9f4fd281106a
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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