Dimethylformamide → HCID 57413952, compound

HRID 532493Notes

Reaction equation

HRID 532493 reaction equation
CN(C)C=O.[F:6][C:7]1[CH:12]=[C:11]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:10]=[CH:9][C:8]=1[C:17]1[C:21]2[N:22]=[CH:23][N:24]=[C:25]([O:26][CH:27]3[CH2:32][CH2:31][N:30]([C:33]#[N:34])[CH2:29][CH2:28]3)[C:20]=2[S:19][CH:18]=1.[NH4+].[Cl-].[N-:37]=[N+:38]=[N-:39].[Na+]>O>[N:34]1[NH:37][N:38]=[N:39][C:33]=1[N:30]1[CH2:31][CH2:32][CH:27]([O:26][C:25]2[C:20]3[S:19][CH:18]=[C:17]([C:8]4[CH:9]=[CH:10][C:11]([S:13]([CH3:16])(=[O:14])=[O:15])=[CH:12][C:7]=4[F:6])[C:21]=3[N:22]=[CH:23][N:24]=2)[CH2:28][CH2:29]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 57415608HCID 57415608, compound

Product 1

HCID 57413952HCID 57413952, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.5 ml of dimethylformamide was added to 200 mg 4-(7-(2-fluoro-4-methanesulfonyl-phenyl)thieno[3,2-d]pyrimidin-4-yloxy)piperidin-1-carbonitrile of Example 75, and 33 mg of NH4Cl and 45 mg of NaN3 45 mg were added thereto with stirring. The mixture was stirred at 100° C. for 12 hr. The resulting mixture was cooled to room temperature, added with water and stirred. The solid thus obtained was filtered to obtain 120 mg of the title compound.

Workup

  1. additionwere added
  2. stirringThe mixture was stirred at 100° C. for 12 hr
  3. stirringstirred
  4. customThe solid thus obtained
  5. filtrationwas filtered

Sources & evidence

ORD record
ord-e74ec1e36d594ff683a76dcf7726e765
Source dataset
uspto-grants-2014_10
Patent number
US08853213B2

Reaction notes

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