Hydrochloric Acid → HCID 67129957, 화합물

HRID 1038829

반응식

HRID 1038829 반응식
[Si]([O:8][CH2:9][CH2:10][C:11]1([CH2:40][NH:41]C(=O)OC(C)(C)C)[CH2:16][CH2:15][N:14]([C:17]2[C:18]3[O:39][CH:38]=[CH:37][C:19]=3[N:20]=[C:21]([NH:23][C:24]3[CH:36]=[CH:35][C:27]4[O:28][C:29]([CH3:34])([CH3:33])[C:30](=[O:32])[NH:31][C:26]=4[CH:25]=3)[N:22]=2)[CH2:13][CH2:12]1)(C(C)(C)C)(C)C.ICCO.CC([Si](Cl)(C)C)(C)C.C(N1CCC(C#N)CC1)C1C=CC=CC=1.C([Si](OCCI)(C)C)(C)(C)C.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.ClC1N=C(Cl)C2OC=CC=2N=1.NC1C=CC2OC(C)(C)C(=O)NC=2C=1.Cl>O1CCOCC1>[NH2:41][CH2:40][C:11]1([CH2:10][CH2:9][OH:8])[CH2:16][CH2:15][N:14]([C:17]2[C:18]3[O:39][CH:38]=[CH:37][C:19]=3[N:20]=[C:21]([NH:23][C:24]3[CH:36]=[CH:35][C:27]4[O:28][C:29]([CH3:34])([CH3:33])[C:30](=[O:32])[NH:31][C:26]=4[CH:25]=3)[N:22]=2)[CH2:13][CH2:12]1

참가 물질

11

반응물 9

HCID 313Hydrochloric AcidHCID 12225IodoethanolHCID 28928tert-Butyldimethylsilyl chlorideHCID 90495Di-tert-butyl dicarbonateHCID 7933831-Benzylpiperidine-4-carbonitrileHCID 11129873tert-Butyl(2-iodoethoxy)dimethylsilaneHCID 136654966-Amino-2,2-dimethyl-2H-1,4-benzoxazin-3(4H)-oneHCID 457899682,4-Dichlorofuro[3,2-D]pyrimidineHCID 70141889tert-Butyl (4-(2-(tert-butyldimethylsilyloxy)ethyl)-1-(2-(2,2-dimethyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-ylamino)furo[3,2-d]pyrimidin-4-yl)piperidin-4-yl)methylcarbamate

생성물 1

HCID 67129957HCID 67129957, 화합물수율 43%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

tert-Butyl (4-(2-(tert-butyldimethylsilyloxy)ethyl)-1-(2-(2,2-dimethyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-ylamino)furo[3,2-d]pyrimidin-4-yl)piperidin-4-yl)methylcarbamate (0.40 g, 0.587 mmol, prepared using AH from 2-iodoethanol with TBDMSCl, AF with 1-benzylpiperidine-4-carbonitrile [Ryan] with tert-butyl(2-iodoethoxy)dimethylsilane, AE, O with Boc2O, G, A with 2,4-dichlorofuro[3,2-d]pyrimidine [ArkPharm] and B with 6-amino-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one [Arkpharm]) and an aqueous solution of aqueous HCl (4 M, 7.34 mL, 29.4 mmol) were dissolved in 1,4-dioxane (15 mL) and stirred for about 4 h at rt. The mixture was concentrated under vacuum and the residue was purified by Prep-TLC (EtOAc/pet ether 1:2) to give 6-(4-(4-(aminomethyl)-4-(2-hydroxyethyl)piperidin-1-yl)furo[3,2-d]pyrimidin-2-ylamino)-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3 (4H)-one (0.121 g, 43%): LC/MS (Table 2, Method h) Rt=1.69 min.; MS m/z: 467 (M+H)+. Syk IC50=A

후처리

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residue was purified by Prep-TLC (EtOAc/pet ether 1:2)

출처 및 근거

ORD 기록
ord-081ab9a8269a4e048fe16760cbaa8de9
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551981B2

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