Trifluoroacetic acid → HCID 67521016, compound

HRID 1926378Notes

Reaction equation

HRID 1926378 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([N:9]2[CH:13]=[C:12]([C:14]3[CH:15]=[C:16]([C:21]4[S:22][C:23]5[C:29]([C:30]6[CH:31]=[N:32]N[CH:34]=6)=[CH:28][CH:27]=[CH:26][C:24]=5[N:25]=4)[C:17]([NH2:20])=[N:18][CH:19]=3)[CH:11]=[N:10]2)[CH2:5][CH2:4]1.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>C(Cl)Cl>[F:38][C:37]([F:40])([F:39])[C:35]([OH:41])=[O:36].[NH:3]1[CH2:8][CH2:7][CH:6]([N:9]2[CH:13]=[C:12]([C:14]3[CH:15]=[C:16]([C:21]4[S:22][C:23]5[C:29]([C:30]6[CH:34]=[CH:35][NH:32][CH:31]=6)=[CH:28][CH:27]=[CH:26][C:24]=5[N:25]=4)[C:17]([NH2:20])=[N:18][CH:19]=3)[CH:11]=[N:10]2)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67521238HCID 67521238, compound

Product 1

HCID 67521016HCID 67521016, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure for 5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-3-[7-(1H-pyrazol-4-yl)benzothiazol-2-yl]pyridin-2-ylamine dihydrochloride was followed, except that TFA in DCM was used for removing the Boc group. 1H NMR (400 MHz, CD3OD): δ=2.24-2.43 (m, 4H), 3.19-3.29 (m, 2H), 3.60 (d, J=13.1 Hz, 2H), 4.60 (ddd, J=10.2, 5.3, 5.2 Hz, 1H), 6.66 (q, J=2.5 Hz, 1H), 6.92 (q, J=2.7 Hz, 1H), 7.28-7.36 (m, 1H), 7.55 (t, J=7.8 Hz, 1H), 7.59-7.65 (m, 1H), 7.86-7.93 (m, 1H), 8.00 (s, 1H), 8.19-8.31 (m, 2H), 8.57 (d, J=2.0 Hz, 1H), 10.76 (br. s., 1H). MS (ES+): m/z=442.19 (100) [MH+]. HPLC: tR=2.38 min (ZQ3, polar—5 min).

Workup

  1. customfor removing the Boc group
  2. custom5 min

Sources & evidence

ORD record
ord-7ba815b832ac45ae865c41b8cf29c893
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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