1-Aminoindane, (S)- → (1S,2S,4R)-4-({6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}amino)-2-(hydroxymethyl)cyclopentanol

HRID 447591Notes

Reaction equation

HRID 447591 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]2[CH2:13][C@H:12]([OH:14])[C@H:11]([CH2:15][OH:16])[CH2:10]2)[CH:3]=1.ClC1N=CN=C(N[C@H]2C[C@@H]3OC(C4C=CC(OC)=CC=4)OC[C@@H]3C2)C=1.[NH2:42][C@@H:43]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH2:45][CH2:44]1>C(O)CCC>[C@@H:43]1([NH:42][C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]3[CH2:13][C@H:12]([OH:14])[C@H:11]([CH2:15][OH:16])[CH2:10]3)[CH:3]=2)[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH2:45][CH2:44]1

Participants

5

Reactant 3

HCID 70000841-Aminoindane, (S)-HCID 59671353(1S,2S,4R)-4-[(6-Chloropyrimidin-4-yl)amino]-2-(hydroxymethyl)cyclopentanolHCID 596713556-chloro-N-[(4aS,6R,7aS)-2-(4-methoxyphenyl)-hexahydrocyclopenta[d][1,3]dioxin-6-yl]pyrimidin-4-amine

Product 1

HCID 66797862(1S,2S,4R)-4-({6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]pyrimidin-4-yl}amino)-2-(hydroxymethyl)cyclopentanolYield 168%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of (1S,2S,4R)-4-[(6-chloropyrimidin-4-yl)amino]-2-(hydroxymethyl)cyclopentanol (33.1 mg, 0.136 mmol), 6-chloro-N-[(4aS,6R,7aS)-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-6-yl]pyrimidin-4-amine (81.6 mg, 0.226 mmol), (S)-(+)-1-aminoindan (0.222 mL, 1.73 mmol) and 1-butanol (1.00 mL) was heated to 180° C. for 6 h in a sealed tube using MWI. The reaction was purified via silica gel chromatography eluting with a gradient of 0 to 15% MeOH in DCM to afford the title compound (77.8 mg, 63%). LC/MS: Rt=1.29 min, ES+ 341 (AA standard).

Workup

  1. customThe reaction was purified via silica gel chromatography
  2. washeluting with a gradient of 0 to 15% MeOH in DCM

Sources & evidence

ORD record
ord-0291062d70bd45aaa0b7a6ee672e48de
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

Loading…