(3,4-Dichlorophenyl)(oxazol-5-yl)methanamine hydrochloride → (R)-tert-butyl 3-(3-fluoro-4-(trifluoromethyl)phenyl)-3-(2-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxamido)propylcarbamate

HRID 2279536Notes

Reaction equation

HRID 2279536 reaction equation
[NH2:1][C@@H:2]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[C:15]([F:23])[CH:14]=1)[CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].O1C[CH2:28][CH:27]([NH:30][C:31]2[N:32]=[CH:33][C:34]3[CH2:40][CH2:39][NH:38][CH2:37][C:35]=3[N:36]=2)[CH2:26]C1.Cl.ClC1C=C(C(C2[O:56][CH:55]=NC=2)N)C=CC=1Cl>>[F:23][C:15]1[CH:14]=[C:13]([C@H:2]([NH:1][C:55]([N:38]2[CH2:39][CH2:40][C:34]3[CH:33]=[N:32][C:31]([NH:30][CH:27]([CH3:26])[CH3:28])=[N:36][C:35]=3[CH2:37]2)=[O:56])[CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:9])[CH3:10])[CH:18]=[CH:17][C:16]=1[C:19]([F:20])([F:21])[F:22]

Participants

4

Reactant 3

HCID 68294638(3,4-Dichlorophenyl)(oxazol-5-yl)methanamine hydrochlorideHCID 71743546N-(tetrahydro-2H-pyran-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-amineHCID 86705529(R)-tert-butyl 3-amino-3-(3-fluoro-4-(trifluoromethyl)phenyl)propylcarbamate

Product 1

HCID 68294477(R)-tert-butyl 3-(3-fluoro-4-(trifluoromethyl)phenyl)-3-(2-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxamido)propylcarbamateYield 39%

Procedure

Condensation of 290 and 72 was carried out in accord with the procedure described in step 6 of example 1 except 290 was used in place of 28 and 72 was used in place of 22. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH gradient (500:8 to 500:15) to afford 0.090 g (39.0%) of (R)-tert-butyl 3-(3-fluoro-4-(trifluoromethyl)phenyl)-3-(2-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxamido)propylcarbamate (292).

Workup

  1. customThe crude product was purified by SiO2 chromatography
  2. washeluting with DCM/MeOH gradient (500:8 to 500:15)

Sources & evidence

ORD record
ord-07a7a4ca353b4cd1b57309be3527d71e
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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