3-Amino-1-propanol → HCID 54689840, compound

HRID 1244135Notes

Reaction equation

HRID 1244135 reaction equation
[Cl:1][C:2]1[S:14][C:5]2[NH:6][C:7](=[O:13])[C:8]([C:11]#[N:12])=[C:9]([OH:10])[C:4]=2[C:3]=1[C:15]1[CH:25]=[CH:24][C:18]([O:19][CH2:20][C:21]([OH:23])=O)=[CH:17][CH:16]=1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:51][CH2:52][CH2:53][CH2:54][OH:55]>>[Cl:1][C:2]1[S:14][C:5]2[NH:6][C:7](=[O:13])[C:8]([C:11]#[N:12])=[C:9]([OH:10])[C:4]=2[C:3]=1[C:15]1[CH:16]=[CH:17][C:18]([O:19][CH2:20][C:21]([NH:51][CH2:52][CH2:53][CH2:54][OH:55])=[O:23])=[CH:24][CH:25]=1

Participants

5

Reactant 4

HCID 90863-Amino-1-propanolHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 54689864HCID 54689864, compound

Product 1

HCID 54689840HCID 54689840, compound

Procedure

A suspension of 2-[4-(2-chloro-5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenoxy]acetic acid (35 mg, 0.093 mmol), HOBt (13 mg, 0.093 mmol), PS-DCC (88 m, 0.121 mmol, 1.37 mmol/g loading), and 3-amino-propan-1-ol (7 mg, 0.0098 mmol) were shaken in a vial at 50 C for 18 h. The reaction was then filtered through celite, eluting with MeOH, and the eluent was concentrated under reduced pressure. The residue was purified by RP-HPLC to give the title compound. MS (ESI) m/e 432 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.60 (m, 2H), 3.21 (m, 2H), 3.42 (t, J=6.27 Hz, 2H), 4.49 (s, 2H), 6.95 (d, J=8.81 Hz, 2H), 7.23 (d, J=8.81 Hz, 2H), 8.11 (m, 1H).

Workup

  1. filtrationThe reaction was then filtered through celite
  2. washeluting with MeOH
  3. concentrationthe eluent was concentrated under reduced pressure
  4. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-6b869a43dc0f436499ed15c0602d0893
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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