Hydrochloric Acid → HCID 136342133, compound

HRID 748547Notes

Reaction equation

HRID 748547 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([C:15]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:24]5[S:25][CH:26]=[CH:27][CH:28]=5)[CH:22]=4)[NH:17][C:16]=3[OH:29])=[N+:12]([O-])[CH:13]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.P(Cl)(Cl)[Cl:31].Cl>C(Cl)(Cl)Cl.CO.C(OCC)C>[ClH:31].[N:1]1([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([C:15]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([C:24]5[S:25][CH:26]=[CH:27][CH:28]=5)[CH:22]=4)[NH:17][C:16]=3[OH:29])=[N:12][CH:13]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24387Phosphorus trichlorideHCID 178526265HCID 178526265, compound

Product 1

HCID 136342133HCID 136342133, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21584188Chloroform methanolSolvent

Procedure

The title compound was prepared as described for Example 86 using 3-[5-(morpholin-4-ylmethyl)-1-oxidopyridin-2-yl]-5-thien-2-yl-1H-indol-2-ol and phosphorus trichloride. The base was dissolved in chloroform/methanol, (3:1), and a solution of HCl in diethyl ether (1 M) was added until acidic pH. The formed precipitation was filtered, washed with diethyl ether and dried. Yield: 9% of the title compound as an yellow solid: 1H NMR (DMSO-d6, 400 MHz) δ 11.10 (br s, 1 H), 10.55 (s, 1 H), 8.21 (s, 1 H), 8.02-7.90 (m, 1 H), 7.85-7.62 (m, 2 H), 7.54-7.46 (m, 1 H), 7.46-7.37 (m, 1 H), 7.18 (d, J=8 Hz, 1 H), 7.15-7.06 (m, 1 H), 6.92 (d, J=8 Hz, 1 H), 4.24 (s, 2 H), 4.03-3.89 (m, 2 H), 3.84-3.51 (m, 2 H), 3.39-3.28 (m, 2 H) 3.16-3.05 (m, 2 H); MS (ES) m/s 392 (M++1).

Workup

  1. customThe title compound was prepared
  2. customThe formed precipitation
  3. filtrationwas filtered
  4. washwashed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-7eb954bb72e94341b71d4fad271ec203
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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