5-Methoxyindoleacetic acid → HCID 177711155, compound

HRID 1819690Notes

Reaction equation

HRID 1819690 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][C:13]([OH:15])=[O:14].C(Cl)Cl.CC#N.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:55]([NH:62][C:63](=[NH:66])[S:64][CH3:65])([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56]>>[C:5]([N:62]([C:55]([O:57][C:58]([CH3:60])([CH3:61])[CH3:59])=[O:56])[C:63](=[NH:66])[S:64][CH3:65])([CH3:9])([CH3:6])[CH3:4].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][C:13]([O:15][C:55](=[O:56])[NH:62][C:63]([S:64][CH3:65])=[NH:66])=[O:14]

Participants

5

Reactant 4

HCID 189865-Methoxyindoleacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86611041HCID 86611041, compoundHCID 137319820tert-butyl N-[(methylsulfanyl)methanimidoyl]carbamate

Product 1

HCID 177711155HCID 177711155, compoundYield 98.6%

Procedure

Step 2 (A): To a mixture of 2-(5-methoxy-1H-indol-3-yl)acetic acid (205 mg, 1.0 mmol)) and CH2Cl2/CH3CN/DIPEA (4.0 mL/0.5 mL/0.5 mL) was added HATU (418 mg, 1.1 mmol). The mixture was stirred at rt for 5 min, and then N-Boc-S-methylisothiourea (preparation C, 190 mg, 1.0 mmol) was added. The reaction was stirred at rt overnight. The resulting crude product was purified by silica gel chromatography to give 280 mg (yield 74%) of tert-butyl N-Boc-S-methylisothiourea-(2-(5-methoxy-1H-indol-3-yl)acetyl)(methylthio)-carbonoimidoylcarbamate. MS (ESI) (M+H)+=378.08. 1H-NMR (500 MHz, CDCl3) δ 7.22 (d, J=8.85 Hz, 1 H), 7.13 (s, 1 H), 6.92-6.99 (m, 1 H), 6.85 (dd, J=8.70, 2.29 Hz, 1 H), 3.83 (s, 5 H), 2.31 (s, 3 H), 1.26-1.51 (m, 9 H).

Workup

  1. stirringThe reaction was stirred at rt overnight
  2. customThe resulting crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1fbb15f423164b16b4207d36d948e558
Source dataset
uspto-grants-2009_10
Patent number
US07601751B2

Reaction notes

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