Toluene → HCID 44231130, compound

HRID 1468567Notes

Reaction equation

HRID 1468567 reaction equation
C(OC([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)=[CH:11][N:10]=[C:9]1[NH:27]C(OC(C)(C)C)=O)=O)(C)(C)C.FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>ClCCl>[C:21]1([C:20]#[C:19][C:16]2[CH:17]=[CH:18][C:13]([C:12]3[NH:8][C:9]([NH2:27])=[N:10][CH:11]=3)=[CH:14][CH:15]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 24970980HCID 24970980, compound

Product 1

HCID 44231130HCID 44231130, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-tert-butoxycarbonylamino-5-(4-phenylethynylphenyl)imidazole-1-carboxylic acid tert-butyl ester (0.039 g, 0.109 mmol) was dissolved in anhydrous dichloromethane (5 mL) and cooled to 0° C. Trifluoroacetic acid (0.250 mL) was added drop-wise while the reaction continued to stir at 0° C. Upon completion, the reaction was allowed to warm to room temperature over the course of 12 h. Toluene (2 mL) was added and the reaction was evaporated to dryness. The crude TFA salt was then dissolved in dichloromethane (3 mL) and a 2M solution of HCl in diethyl ether (0.10 mL) was added. The solution was again concentrated under reduced pressure and the resulting product triturated with cold diethyl ether (5 mL) to afford 0.031 g (97%) of 5-(4-phenylethynylphenyl)-1H-imidazol-2-ylamine in its corresponding hydrochloride salt form as a brown solid: 1H NMR (300 MHz, DMSO-d6) δ 13.06 (s, 1H), 12.27 (s, 1H), 7.74 (d, 2H, J=8.7 Hz), 7.62 (d, 2H, J=8.7 Hz), 7.55 (m, 5H), 7.43 (m, 3H); 13C NMR (75 MHz, DMSO-d6) δ 147.9, 131.9, 131.2, 128.9, 128.7, 127.9, 125.7, 124.3, 122.1, 121.4, 110.6, 90.3, 89.0; HRMS (ESI) calcd for C17H13N3 (M+) 259.1110. found 259.1113.

Workup

  1. temperatureto warm to room temperature over the course of 12 h
  2. customthe reaction was evaporated to dryness
  3. dissolutionThe crude TFA salt was then dissolved in dichloromethane (3 mL)
  4. additiona 2M solution of HCl in diethyl ether (0.10 mL) was added
  5. concentrationThe solution was again concentrated under reduced pressure
  6. customthe resulting product triturated with cold diethyl ether (5 mL)

Sources & evidence

ORD record
ord-7bbac10df90f40ffa55bc686892e7387
Source dataset
uspto-grants-2015_04
Patent number
US09005643B2

Reaction notes

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