Hydrochloric Acid → HCID 57463080, compound

HRID 1783846Notes

Reaction equation

HRID 1783846 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15]2[N:20]=[C:19]([C:21]3[N:28]4[C:24]([S:25][CH:26]=[CH:27]4)=[N:23][C:22]=3[C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]4[N:39]=[C:38]([CH3:40])[O:37][N:36]=4)[CH:30]=3)[CH:18]=[CH:17][N:16]=2)[CH2:9]1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[CH3:40][C:38]1[O:37][N:36]=[C:35]([C:31]2[CH:30]=[C:29]([C:22]3[N:23]=[C:24]4[N:28]([C:21]=3[C:19]3[CH:18]=[CH:17][N:16]=[C:15]([NH:14][C@@H:10]5[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]5)[N:20]=3)[CH:27]=[CH:26][S:25]4)[CH:34]=[CH:33][CH:32]=2)[N:39]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57590729HCID 57590729, compound

Product 1

HCID 57463080HCID 57463080, compoundYield 109.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

((R)-3-(4-{6-[3-(5-Methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-imidazo[2,1-b]thiazol-5-yl}-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (0.15 g, 0.269 mmol) was dissolved in 2 mL of ethyl acetate and treated with 2 ml of 3.0 M HCl in ethyl acetate at room temperature (RT) overnight. Solid product was filtered, washed ethyl acetate and dried under vacuum overnight to provide 0.135 g (100%) of the title compound as a yellow solid. M.p.=203-207° C. 400 MHz 1H NMR (DMSO-d6 at 60° C.) δ: 9.35 (br. s, 1H), 8.21 (s, 1H), 8.12 (d, J=6.0 Hz, 1H), 8.0 (d, J=7.6 Hz, 1H), 7.82-7.80 (m, 1H), 7.67 (t, J=8.2 Hz, 1H), 7.54 (s, 1H), 6.90 (bs, 1H), 6.48 (d, J=5.6 Hz, 1H), 4.2 (br. s, 1H), 3.40 (d, J=10.8 Hz, 1H), 3.13 (d, 1H), 2.92-2.87 (m, 2H), 2.65 (s, 3H), 2.00-1.97 (m, 1H), 1.96-1.89 (m, 1H), 1.89-1.80 (bs, 1H), 1.64-1.57 (m, 1H); LCMS: 459 [M+H]. calc. for C23H22N8OS.2.3HCl: C, 50.93; H, 4.52; N, 20.66. Found C, 50.93; H, 4.42; N, 19.30.

Workup

  1. filtrationSolid product was filtered
  2. washwashed ethyl acetate
  3. customdried under vacuum overnight

Sources & evidence

ORD record
ord-a248a620d0164213b25a65efa3042531
Source dataset
uspto-grants-2009_03
Patent number
US07501430B2

Reaction notes

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