3-Amino-1-propanol → AZD-9056 hydrochloride

HRID 719661Notes

Reaction equation

HRID 719661 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][CH:38]=O)=[CH:32][C:17]=1[C:18]([NH:20][CH2:21][C:22]12[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH2:23]1)[CH2:29]2)=[O:19].[NH2:40][CH2:41][CH2:42][CH2:43][OH:44]>ClCCl>[ClH:15].[Cl:15][C:16]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][CH2:38][NH:40][CH2:41][CH2:42][CH2:43][OH:44])=[CH:32][C:17]=1[C:18]([NH:20][CH2:21][C:22]12[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH2:23]1)[CH2:29]2)=[O:19]

Participants

5

Reactant 3

HCID 90863-Amino-1-propanolHCID 5049666Sodium triacetoxyborohydrideHCID 120853482-Chloro-5(3-oxopropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Product 1

HCID 10161380AZD-9056 hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (4.10 g) was added to a solution of 2-chloro-5-(3-oxopropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (3.46 g, Example 14b) and 3-aminopropanol (1.73 ml) in dichloromethane (200 ml). After 24 h the crude reaction mixture was purified by flash chromatography (eluting with 5–20% methanol/dichloromethane+1% ammonia) and the hydrochloride salt precipitated from ether/methanol 19:1, to afford the title compound as a white solid (1.60 g).

Workup

  1. customAfter 24 h the crude reaction mixture
  2. customwas purified by flash chromatography (eluting with 5–20% methanol/dichloromethane+1% ammonia)
  3. customthe hydrochloride salt precipitated from ether/methanol 19:1

Sources & evidence

ORD record
ord-504271022fec48fb886405e4385ea000
Source dataset
uspto-grants-2006_11
Patent number
US07132457B2

Reaction notes

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