Hydrochloric Acid → HCID 69919768, compound

HRID 1006290Notes

Reaction equation

HRID 1006290 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([NH:20][CH2:21][CH:22]4[CH2:24][CH2:23]4)[CH:18]=3)[N:13]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=3)[C:12]=2[C:34]([O:36]CC)=[O:35])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[ClH:39]>>[ClH:39].[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([NH:20][CH2:21][CH:22]4[CH2:24][CH2:23]4)[CH:18]=3)[N:13]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=3)[C:12]=2[C:34]([OH:36])=[O:35])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 22676744HCID 22676744, compound

Product 1

HCID 69919768HCID 69919768, compoundYield 59%

Procedure

Ethyl 3(4-tert-butylphenyl)-5-[(cyclopropylmethyl)amino]-1-(3-methoxybenzyl)-1H-indole-2-carboxylate (Example 165, 420 mg, 0.84 mmol) was reacted using the method described for Example 237. After hydrolysis the solution was adjusted to pH=1 using 1 M hydrochloric acid. The resulting precipitate was collected by filtration, using ethyl ether to wash, to afford 250 mg, (59%) of product. The product had: 1H NMR (300 MHz, CD3OD) δ 7.71 (d, 1 H), 7.39-7.59 (m, 6 H), 7.16 (dd, 1 H), 6.72-6.80 (m, 1 H), 6.61-6.69 (m, 2 H), 5.84 (s, 2 H), 4.36 (s, 2 H), 3.71 (s, 3 H), 2.68-2.80 (m, 1 H), 1.41 (s, 9 H), 1.15-1.25 (m, 1 H), 0.80-0.96 (m, 4 H); mass spectroscopy gave MH+−HCl=483.3 (calcd exact mass for C31H34N2O3=482.26).

Workup

  1. customAfter hydrolysis the solution
  2. filtrationThe resulting precipitate was collected by filtration
  3. washto wash

Sources & evidence

ORD record
ord-a24a079731ec4abd9eb88330e68b29cd
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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