Trifluoroacetic acid → HCID 59679923, compound

HRID 1697134Notes

Reaction equation

HRID 1697134 reaction equation
COC1C=CC(C[NH:8][C:9]2[C:14]([C:15]3[N:16]=[C:17]4[N:21]([CH:22]=3)[C:20]([CH2:23][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:19][S:18]4)=[CH:13][CH:12]=[CH:11][N:10]=2)=CC=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[N:24]1([CH2:23][C:20]2[N:21]3[CH:22]=[C:15]([C:14]4[C:9]([NH2:8])=[N:10][CH:11]=[CH:12][CH:13]=4)[N:16]=[C:17]3[S:18][CH:19]=2)[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 12052TriethylsilaneHCID 59680069(4-Methoxy-benzyl)-[3-(3-morpholin-4-ylmethyl-imidazo[2,1-b]thiazol-6-yl)-pyridin-2-yl]-amine

Product 1

HCID 59679923HCID 59679923, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Methoxy-benzyl)-[3-(3-morpholin-4-ylmethyl-imidazo[2,1-b]thiazol-6-yl)-pyridin-2-yl]-amine (100 mg, 0.23 mmol) was mixed with 2 mL of CH2Cl2 along with triethylsilane (0.11 mL, 2 eq). Trifluoroacetic acid (1 mL) was added and the reaction mixture was stirred at room temperature for 18 hours. The following day, the reaction mixture was concentrated. The resulting residue was triturated with Et2O to afford essentially quantitative yield of 3-(3-morpholin-4-ylmethyl-imidazo[2,1-b]thiazol-6-yl)-pyridin-2-ylamine as the TFA salt.

Workup

  1. concentrationThe following day, the reaction mixture was concentrated
  2. customThe resulting residue was triturated with Et2O

Sources & evidence

ORD record
ord-f4c58a04588f43b8b007ef98aa564706
Source dataset
uspto-grants-2012_04
Patent number
US08163908B2

Reaction notes

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