Dichloromethane → HCID 86634763, compound

HRID 911044Notes

Reaction equation

HRID 911044 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([NH:12][C:13]3[N:18]=[CH:17][C:16]([S:19][CH2:20][CH:21]4[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]4)=[C:15]([O:34][C:35]4[CH:44]=[CH:43][CH:42]=[C:41]5[C:36]=4[CH:37]=[CH:38][CH:39]=[N:40]5)[CH:14]=3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:53]>>[ClH:53].[ClH:53].[C:1]1([C:7]2[N:8]=[C:9]([NH:12][C:13]3[CH:14]=[C:15]([O:34][C:35]4[CH:44]=[CH:43][CH:42]=[C:41]5[C:36]=4[CH:37]=[CH:38][CH:39]=[N:40]5)[C:16]([S:19][CH2:20][CH:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[CH:17][N:18]=3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 57899016HCID 57899016, compound

Product 1

HCID 86634763HCID 86634763, compoundYield 39.3%

Procedure

A flask was charged with tert-butyl 4-((6-(4-phenylthiazol-2-ylamino)-4-(quinolin-5-yloxy)pyridin-3-ylthio)methyl)piperidine-1-carboxylate (prepared according to the method of Example 202) (0.150 g, 0.240 mmol) and 4 mL DCM. TFA (4 mL) was added and the reaction was stirred at ambient temperature for 2 hours and then concentrated. The crude material was purified on a SCX ion exchange column using DCM, methanol and ammoniated methanol as eluent. The isolated material was treated with 2M HCl (2 mL) in ether and dried to give the title compound (0.057 g, 39.3% yield) as light yellow solid. 1H NMR (DMSO-d6) δ 11.14 (s, 1H), 9.06 (dd, 1H), 8.67 (m, 1H), 8.43 (s, 1H), 8.34 (d, 1H), 8.09 (d, 1H), 7.91 (t, 1H), 7.71 (s, 1H), 7.70 (s, 1H), 7.67 (dd, 1H), 7.50 (d, 1H), 7.43 (s, 1H), 7.31 (t, 2H), 7.28 (m, 1H) 6.58 (s, 1H), 3.25 (m, 2H), 2.95 (d, 2H), 2.86 (m, 2H), 2.01 (m, 2H), 1.80 (m, 1H), 1.40 (m, 2H).

Workup

  1. customprepared
  2. concentrationconcentrated
  3. customThe crude material was purified on a SCX ion exchange column
  4. additionThe isolated material was treated with 2M HCl (2 mL) in ether
  5. customdried

Sources & evidence

ORD record
ord-19365f35543c4830873beab42ed17249
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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