Tetrabutylammonium Fluoride → HCID 71509960, compound

HRID 1499815Notes

Reaction equation

HRID 1499815 reaction equation
Cl.Cl.[NH:3]1[CH2:6][CH:5]([C:7]2[C:8]([O:30][CH2:31][CH3:32])=[C:9]([CH:15]([N:17]3[C:21]4=[N:22][CH:23]=[N:24][C:25]([NH2:26])=[C:20]4[C:19]([CH:27]([F:29])[F:28])=[N:18]3)[CH3:16])[CH:10]=[C:11]([Cl:14])[C:12]=2[F:13])[CH2:4]1.[Si]([O:40][CH2:41][CH:42]=O)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[NH2:26][C:25]1[N:24]=[CH:23][N:22]=[C:21]2[N:17]([CH:15]([C:9]3[C:8]([O:30][CH2:31][CH3:32])=[C:7]([CH:5]4[CH2:6][N:3]([CH2:42][CH2:41][OH:40])[CH2:4]4)[C:12]([F:13])=[C:11]([Cl:14])[CH:10]=3)[CH3:16])[N:18]=[C:19]([CH:27]([F:29])[F:28])[C:20]=12

Participants

4

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 86677737HCID 86677737, compound

Product 1

HCID 71509960HCID 71509960, compound

Procedure

This compound was prepared using procedures analogous to those for Example 1 step 8, with 1-[1-(3-azetidin-3-yl-5-chloro-2-ethoxy-4-fluorophenyl)ethyl]-3-(difluoromethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine dihydrochloride (racemic) and {[tert-butyl(dimethyl)silyl]oxy}acetaldehyde as starting materials. After reductive amination, tetrabutylammonium fluoride was added to remove the tert-butyl(dimethyl)silyl group. The product was isolated as a racemic mixture. LCMS calculated for C21H25ClF3N6O2 (M+H)+: m/z=485.2; Found: 485.2. 1H NMR (300 MHz, DMSO-d6): δ 8.23 (s, 1H), 7.38 (m, 2H), 6.29 (m, 1H), 3.78-3.67 (m, 4H), 3.53 (m, 1H), 3.12 (m, 2H), 2.99-2.87 (m, 2H), 2.34 (m, 2H), 1.68 (d, 3H), 1.22 (m, 3H) ppm.

Workup

  1. customThis compound was prepared
  2. customto remove the tert-butyl(dimethyl)silyl group
  3. customThe product was isolated as a racemic mixture

Sources & evidence

ORD record
ord-eb208f74fcac4e04933edc2b475ce506
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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