Trifluoroacetic acid → 6-(2,7-Diazaspiro[3.5]nonan-7-yl)-4-(5-methyl-1H-pyrazol-3-ylamino)-2-[2-{3-(pyrid-2-yl)isoxazol-5-yl}pyrrolidin-1-yl]pyrimidine

HRID 2105222Notes

Reaction equation

HRID 2105222 reaction equation
C(OC([N:8]1[CH2:11][C:10]2([CH2:16][CH2:15][N:14]([C:17]3[N:22]=[C:21]([N:23]4[CH2:27][CH2:26][CH2:25][CH:24]4[C:28]4[O:32][N:31]=[C:30]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=5)[CH:29]=4)[N:20]=[C:19]([NH:39][C:40]4[CH:44]=[C:43]([CH3:45])[NH:42][N:41]=4)[CH:18]=3)[CH2:13][CH2:12]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>>[CH2:9]1[C:10]2([CH2:16][CH2:15][N:14]([C:17]3[N:22]=[C:21]([N:23]4[CH2:27][CH2:26][CH2:25][CH:24]4[C:28]4[O:32][N:31]=[C:30]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=5)[CH:29]=4)[N:20]=[C:19]([NH:39][C:40]4[CH:44]=[C:43]([CH3:45])[NH:42][N:41]=4)[CH:18]=3)[CH2:13][CH2:12]2)[CH2:11][NH:8]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 688149186-[2-(tert-Butoxycarbonyl)-2,7-diazaspiro[3.5]nonan-7-yl]-4-(5-methyl-1H-pyrazol-3-ylamino)-2-[2-{3-(pyrid-2-yl)isoxazol-5-yl}pyrrolidin-1-yl]pyrimidine

Product 1

HCID 688165596-(2,7-Diazaspiro[3.5]nonan-7-yl)-4-(5-methyl-1H-pyrazol-3-ylamino)-2-[2-{3-(pyrid-2-yl)isoxazol-5-yl}pyrrolidin-1-yl]pyrimidine

Procedure

A mixture of 6-[2-(tert-butoxycarbonyl)-2,7-diazaspiro[3.5]nonan-7-yl]-4-(5-methyl-1H-pyrazol-3-ylamino)-2-[2-{3-(pyrid-2-yl)isoxazol-5-yl}pyrrolidin-1-yl]pyrimidine (Example 147) (110 mg, 0.19 mmol) and TFA (2 ml) were stirred at ambient temperature for 60 minutes. The volatiles were removed by evaporation, the residue dissolved in DCM poured onto an isolute SCX-2 ion exchange column. The column was eluted with methanol to elute any neutrals, followed by 7M methanolic ammonia to elute the product. The solvent was removed by evaporation to afford the desired product as a yellow solid. (66 mg, 68%).

Workup

  1. customThe volatiles were removed by evaporation
  2. dissolutionthe residue dissolved in DCM
  3. additionpoured onto an isolute SCX-2 ion exchange column
  4. washThe column was eluted with methanol
  5. washto elute any neutrals
  6. washto elute the product
  7. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-d72c4e555f7445ebb3e39392856046b8
Source dataset
uspto-grants-2009_08
Patent number
US07579349B2

Reaction notes

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