Ethyl Acetate → HCID 178482367, compound

HRID 1921995Notes

Reaction equation

HRID 1921995 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH3:25])[N:19]=3)[CH:9]=[C:10]2[NH:13][CH2:14][CH2:15][CH2:16][NH2:17])=[CH:5][CH:4]=1.[Br:26][C:27]1[C:35]2[C:30](=[N:31][CH:32]=[N:33][C:34]=2Cl)[NH:29][N:28]=1.C(OCC)(=O)C>O1CCCC1.C(N(CC)CC)C>[Br:26][C:27]1[C:35]2[C:30](=[N:31][CH:32]=[N:33][C:34]=2[NH:17][CH2:16][CH2:15][CH2:14][NH:13][C:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[CH:7]=[C:8]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH3:25])[N:19]=3)[CH:9]=2)[NH:29][N:28]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 67305956N1-(7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl) propane-1,3-diamineHCID 1784783943-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 178482367HCID 178482367, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

To a slurry of 182 in tetrahydrofuran (10 ml) and triethylamine (0.3 ml) was added 3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (63 mg). The mixture was shaken at 50° C. for 24 hours. After cooling to room temperature the mixture was poured into ethyl acetate (150 ml) washed with water (2×200 ml) and the organic layer dried over anhydrous magnesium sulfate. Evaporation to dryness gave a yellow solid which was purified by silica gel chromatography eluting with 60-100% ethyl acetate in hexanes to 1% methanol in ethyl acetate yielding N1-(3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-N3-(7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)propane-1,3-diamine 183 as a yellow powder (43 mg). M.p.=145-148° C. 1H NMR (DMSO-d6) 400 MHz δ 8.26 (s, 1H), 7.84-7.8 (m, 2H), 7.63-7.52 (m, 1H), 7.22-7.0 (m, 5H), 7.15-7.12 (m, 1H), 5.16 (m, 1H), 4.56-4.53 (m, 2H), 3.9 (s, 3H), 3.75 (m, 2H), 3.52-3.4 (m, 2H), 2.87-2.86 (m, 3H), 2.11 (m, 2H), LCMS m/e 534 and 536 (M+) Calculated for C24H24BrN9O 0.72 H2O-0.32 C4H8O2: C 52.75, H 4.9, N 21.9; found C, 52.76; H, 4.44; N, 21.92.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. washwashed with water (2×200 ml)
  3. dry with materialthe organic layer dried over anhydrous magnesium sulfate
  4. customEvaporation to dryness
  5. customgave a yellow solid which
  6. customwas purified by silica gel chromatography
  7. washeluting with 60-100% ethyl acetate in hexanes to 1% methanol in ethyl acetate

Sources & evidence

ORD record
ord-e22734c4df8a41e3828da35d5728f3a6
Source dataset
uspto-grants-2012_05
Patent number
US08173808B2

Reaction notes

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