Trifluoroacetic acid → HCID 58215683, compound

HRID 1630901Notes

Reaction equation

HRID 1630901 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[C:18]([C:20]3[N:21]([CH3:32])[C:22]4[C:27]([C:28]=3[C:29]#[N:30])=[CH:26][CH:25]=[C:24]([Cl:31])[CH:23]=4)[CH:19]=2)[CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:7][C@@H:8]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[C:18]([C:20]3[N:21]([CH3:32])[C:22]4[C:27]([C:28]=3[C:29]#[N:30])=[CH:26][CH:25]=[C:24]([Cl:31])[CH:23]=4)[CH:17]=[N:16][CH:15]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58215540HCID 58215540, compound

Product 1

HCID 58215683HCID 58215683, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {(R)-1-[5-(6-chloro-3-cyano-1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester (140 mg, 0.3 mmol) in dichloromethane (5 mL) is added TFA (2 mL) and the mixture is stirred at room temperature for 2 h. The solvents are then removed in vacuo and the residue is purified by Xbridge C18 with a gradient of acetonitrile in 0.1% NH4OH to give 2-[5-((R)-3-amino-pyrrolidin-1-ylmethyl)-pyridin-3-yl]-6-chloro-1-methyl-1H-indole-3-carbonitrile. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.33-1.43 (m, 1H), 1.64 (br. s., 2H), 1.97-2.08 (m, 1H), 2.21 (dd, J=9.0, 4.9 Hz, 1H), 2.59-2.68 (m, 1H), 2.71 (dd, J=9.1, 6.6 Hz, 1H), 3.32-3.39 (m, 1H), 3.72 (q, J=13.6 Hz, 2H), 3.79 (s, 3H), 7.36 (dd, J=8.3, 1.8 Hz, 1H), 7.72 (d, J=8.6 Hz, 1H), 7.96 (d, J=1.5 Hz, 1H), 8.05 (t, J=2.0 Hz, 1H), 8.72 (d, J=2.0 Hz, 1H), 8.77 (d, J=2.3 Hz, 1H). HRMS (ESI) m/z 366.1483 [(M+H)+ Calcd for C20H21ClN5: 366.1485].

Workup

  1. customThe solvents are then removed in vacuo
  2. customthe residue is purified by Xbridge C18 with a gradient of acetonitrile in 0.1% NH4OH

Sources & evidence

ORD record
ord-1ecda3b88dda4328bf6ffa9e90ccd64c
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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