HCID 58529597, compound → HCID 58529380, compound

HRID 1972823Notes

Reaction equation

HRID 1972823 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:28]3[CH:29]=[CH:30][C:31]4[C:35]([CH:36]=3)=[N:34][N:33]([CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:32]=4)[CH:9]=[C:10]([CH:11]3[O:16][CH2:15][CH:14]4[CH2:17][N:18](C(OC(C)(C)C)=O)[CH2:19][CH2:20][N:13]4[CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1>ClCCl.FC(F)(F)C(O)=O>[CH2:37]([N:33]1[CH:32]=[C:31]2[C:35]([CH:36]=[C:28]([C:8]3[CH:9]=[C:10]([CH:11]4[O:16][CH2:15][CH:14]5[CH2:17][NH:18][CH2:19][CH2:20][N:13]5[CH2:12]4)[N:6]4[C:7]=3[C:2]([NH2:1])=[N:3][CH:4]=[N:5]4)[CH:29]=[CH:30]2)=[N:34]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

4

Reactant 1

HCID 58529597HCID 58529597, compound

Product 1

HCID 58529380HCID 58529380, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred solution of tert-butyl 3-[4-amino-5-(2-benzyl-2H-indazol-6-yl)pyrrolo[2,1-f][1,2,4]triazin-7-yl]hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate (75 mg, 0.13 mmol) in dichloromethane (5 mL), trifluoroacetic acid (1 mL) was added. The reaction was allowed to stir for 30 minutes and concentrated. The mixture was partitioned between ethyl acetate (30 mL) and pH 14 saturated aqueous NaCl (10 mL). The layers were separated and the organic phase was washed, dried (Na2SO4), and concentrated to dryness. The residue was triturated with Et2O to obtain 50 mg (80%) of the desired product. 1H-NMR (DMSO-d6) 8.53 (s, 1H), 7.90 (s, 1H), 7.78 (d, 1H), 7.57 (s, 1H), 7.35-7.28 (m, 5H), 7.11 (d, 1H), 6.70 (s, 1H), 5.64 (s, 2H), 5.11 (d, 1 H), 3.71 (dd, 1 H), 3.33-3.26 (m, 1H), 2.91 (d, 1H), 2.74-2.58 (m, 4H), 2.39 (t, 1H), 2.21-2.00 (m, 4H); LC-MS [M+H]+=481, RT=2.00 min.

Workup

  1. concentrationconcentrated
  2. customThe mixture was partitioned between ethyl acetate (30 mL) and pH 14 saturated aqueous NaCl (10 mL)
  3. customThe layers were separated
  4. washthe organic phase was washed
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to dryness
  7. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-66db6dda0ee8465ab8ccc7d2f5dc4780
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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