Trifluoroacetic acid → HCID 59129572, compound

HRID 468487Notes

Reaction equation

HRID 468487 reaction equation
FC(F)(F)C(O)=O.[O:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]3([C:20]([NH:22][C:23]4[CH:24]=[C:25]5[C:29](=[CH:30][CH:31]=4)[NH:28][C:27]([C:32]([CH3:43])([CH3:42])[CH2:33][NH:34]C(=O)OC(C)(C)C)=[CH:26]5)=[O:21])[CH2:19][CH2:18]3)=[CH:16][C:11]=2[O:10][CH2:9]1>ClCCl>[NH2:34][CH2:33][C:32]([C:27]1[NH:28][C:29]2[C:25]([CH:26]=1)=[CH:24][C:23]([NH:22][C:20]([C:17]1([C:15]3[CH:14]=[CH:13][C:12]4[O:8][CH2:9][O:10][C:11]=4[CH:16]=3)[CH2:19][CH2:18]1)=[O:21])=[CH:31][CH:30]=2)([CH3:42])[CH3:43]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24763146HCID 24763146, compound

Product 1

HCID 59129572HCID 59129572, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.75 mL) was added to a solution of tert-butyl 2-(5-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-1H-indol-2-yl)-2-methylpropylcarbamate (77 mg, 0.16 mmol) in dichloromethane (3 mL) and the mixture was stirred at room temperature for 1.5 h. The mixture was evaporated, dissolved in dichloromethane, washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and evaporated to dryness to give N-(2-(1-amino-2-methylpropan-2-yl)-1H-indol-5-yl)-1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (53 mg, 86%). 1H NMR (400 MHz, CDCl3) δ 9.58 (s, 1H), 7.60 (d, J=1.6 Hz, 1H), 7.18-7.15 (m, 2H), 7.02-6.94 (m, 3H), 6.85 (d, J=7.8 Hz, 1H), 6.14 (d, J=1.2 Hz, 1H), 6.02 (s, 2H), 2.84 (s, 2H), 1.68 (dd, J=3.6, 6.7 Hz, 2H), 1.32 (s, 6H), 1.08 (dd, J=3.7, 6.8 Hz, 2H).

Workup

  1. customThe mixture was evaporated
  2. dissolutiondissolved in dichloromethane
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-e4ab7dc0fc1244f69881deb2aa673821
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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