Dichloromethane → HCID 178432165, compound

HRID 2282284Notes

Reaction equation

HRID 2282284 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([C:25]4[S:26][C:27]([C:36]5[N:40]=[CH:39][N:38](C6CCCCO6)[N:37]=5)=[C:28]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[N:29]=4)=[C:22]([CH3:24])[N:23]=3)[CH:20]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(Cl)Cl>>[CH3:24][C:22]1[N:23]=[C:18]2[CH:17]=[CH:16][C:15]([CH2:14][N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:20][N:19]2[C:21]=1[C:25]1[S:26][C:27]([C:36]2[N:40]=[CH:39][NH:38][N:37]=2)=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:29]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 58095063HCID 58095063, compound

Product 1

HCID 178432165HCID 178432165, compoundYield 47.7%

Procedure

tert-Butyl-4-[(2-methyl-3-{4-phenyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-1,3-thiazol-2-yl}imidazo[1,2-a]pyridin-6-yl)methyl]piperazine-1-carboxylate (0.025 g, 0.039 mmol) was treated with Trifluoroacetic Acid (2.0 mL, 26 mmol) in Methylene chloride (2.0 mL, 31 mmol) at r.t. for 18 hours. The mixture was rotavaped. The residue was triturated with hexane (3×5 mL). The solid residue was suspended in water and neutralized with saturated aqueous NaHCO3 to pH ˜9, extracted with 10% MeOH in DCM (3×10 mL). The combined organic layer was dried over Na2SO4, filtered, rotavaped and dried in hi-vac to give a solid product (0.0085 g, 45% yield). LCMS: (FA) ES+ 457, ES− 455. 1H NMR (400 MHz, d-chroloform & d4-methanol) δ 9.82 (s, 1H), 8.14 (s, 1H), 7.80-7.82 (m, 2H), 7.55-7.58 (m, 1H), 7.37-7.46 (m, 4H), 3.54 (s, 2H), 2.84 (m, 2H), 2.76 (s, 3H), 2.47 (s, br, 2H), 2.32 (m, 4H).

Workup

  1. customThe residue was triturated with hexane (3×5 mL)
  2. extractionextracted with 10% MeOH in DCM (3×10 mL)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customdried in hi-vac

Sources & evidence

ORD record
ord-8f89a00b185b45dfb71fc21cbbbff1a9
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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