Hydrochloric Acid → HCID 67519766, compound

HRID 1925218Notes

Reaction equation

HRID 1925218 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]3[N:15]([C:16]=2[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C@@H:24]4[CH2:29][CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]4)[N:18]=2)[CH:14]=[CH:13][S:12]3)[CH:6]=[CH:7][CH:8]=1.[ClH:37]>O1CCOCC1.CCOCC>[ClH:37].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]3[N:15]([C:16]=2[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C@@H:24]4[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]4)[N:18]=2)[CH:14]=[CH:13][S:12]3)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57463068HCID 57463068, compound

Product 1

HCID 67519766HCID 67519766, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

The tert-butyl (3R)-3-({4-[6-(3-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]pyrimidin-2-yl}amino)piperidine-1-carboxylate (21 g, 41.5 mmol) is dissolved in 250 ml of dioxane and treated with 75 ml of anhydrous a four molar HCl in dioxane at room temperature (RT). The reaction mixture is stirred at room temperature for three hours. The mixture is then diluted with 350 ml of ether and stirred until product separates as a solid. Solid product is filtered and washed with ether. The solid is dissolved in MeOH (200 ml) and concentrated to dryness twice. The product is dried at high vacuum to yield 20.275 g of yellow solid (tris HCl salt) (90%). M.p.=220-225° C.; 300 MHz 1H NMR (DMSO-d6 at 80° C.) δ: 9.6-9.3 (br. s, 2H), 8.9-8.4 (br. s, 2H), 8.82 (s, 1H), 8.11 (d, J=5.8 Hz, 1H), 7.50 (d, J=4.7 Hz, 1H), 7.39 (t, J=7.98 Hz, 1H), 7.2-7.1 (m, 2H), 7.08-7.0 (m, 1H), 6.49 (d, J=5.8 Hz, 1H), 4.4-4.3 (m, 1H), 3.79 (s, 3H), 3.39 (d, J=10.2 Hz, 1H), 3.16 (br. s, 1H), 3.05-2.7 (m, 2H), 2.2-1.6 (m, 3H), 1.55-1.2 (m, 1H). LCMS: 407 [M+H]; calc. for C21H22N6OS 3.3 HCl 0.05 dioxane 0.3 methanol: C, 47.75; H, 5.01; N, 15.54; found. C, 47.73; H, 5.26; N, 15.55.

Workup

  1. stirringstirred until product separates as a solid
  2. filtrationSolid product is filtered
  3. washwashed with ether
  4. dissolutionThe solid is dissolved in MeOH (200 ml)
  5. concentrationconcentrated to dryness twice
  6. customThe product is dried at high vacuum

Sources & evidence

ORD record
ord-f17f8bc906484f31889d9b8430c1b23c
Source dataset
uspto-grants-2012_05
Patent number
US08178672B2

Reaction notes

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