Trifluoroacetic acid → HCID 58529458, compound

HRID 1973029Notes

Reaction equation

HRID 1973029 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[N:29]3[C:24]([C:25]([NH2:30])=[N:26][CH:27]=[N:28]3)=[C:23]([C:31]3[CH:32]=[CH:33][C:34]4[C:38]([CH:39]=3)=[N:37][N:36]([CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:35]=4)[CH:22]=2)[CH2:17][CH2:16]1)=[O:14])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:40]([N:36]1[CH:35]=[C:34]2[C:38]([CH:39]=[C:31]([C:23]3[CH:22]=[C:21]([CH:18]4[CH2:17][CH2:16][N:15]([C:13](=[O:14])[C@@H:9]5[CH2:10][CH2:11][CH2:12][NH:8]5)[CH2:20][CH2:19]4)[N:29]4[C:24]=3[C:25]([NH2:30])=[N:26][CH:27]=[N:28]4)[CH:32]=[CH:33]2)=[N:37]1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69327386HCID 69327386, compound

Product 1

HCID 58529458HCID 58529458, compoundYield 17.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{4-[4-Amino-5-(2-benzyl-2H-indazol-6-yl)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-piperidine-1-carbonyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (73.5 mg, 0.1 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (0.2 mL). The reaction was stirred at rt for 5 h. The sample was concentrated and the residue taken up in 1.5 mL of methanol, 0.5 mL of acetonitrile and 0.5 mL of water. The sample was then free-based using Phenomenex's Strata-X-C cation mixed mode polymer SPE plate (500 mg/6 mL/well) to give 9.20 mg (17%) of desired product. 1H NMR (400 MHz, DMSO-d6) δ 8.54 (s, 1 H), 7.80 (d, J=8.56 Hz, 1 H), 7.60 (s, 1 H), 7.29-7.39 (m, 5 H), 7.15 (d, J=8.56 Hz, 1 H), 6.63 (d, J=11.49 Hz, 1 H), 4.52 (d, J=12.59 Hz, 1 H), 4.05 (d, J=11.62 Hz, 1 H), 2.78 (t, J=12.47 Hz, 1 H), 2.56-2.66 (m, 1 H), 2.17 (s, 1 H), 1.99-2.10 (m, 5 H), 1.77-1.85 (m, 5 H), 1.63-1.69 (m, 2 H), 1.52-1.62 (m, 3 H), 1.17-1.27 (m, 2 H); MS LC-MS [M+H]+=521.5, RT=2.96 min.

Workup

  1. concentrationThe sample was concentrated
  2. additionmixed mode polymer SPE plate (500 mg/6 mL/well)

Sources & evidence

ORD record
ord-b534246f8943480fbc6fb044b986bf5c
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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