Ammonium Acetate → HCID 178493034, 화합물

HRID 592060노트

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HRID 592060 반응식
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][C@@H:10]2[C@@H:15]3[O:16][C@@H:12]([CH2:13][CH2:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])[C:5]([Cl:20])=[CH:4][N:3]=1.[CH3:21][O:22][C:23]1[CH:30]=[C:29]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[CH:28]=[CH:27][C:24]=1[CH:25]=O.C([O-])(=O)C.[NH4+]>CCO>[Cl:20][C:5]1[C:6]([NH:9][C@@H:10]2[C@@H:15]3[O:16][C@@H:12]([CH2:13][CH2:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])=[C:7]2[N:8]=[C:25]([C:24]3[CH:27]=[CH:28][C:29]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)=[CH:30][C:23]=3[O:22][CH3:21])[NH:1][C:2]2=[N:3][CH:4]=1

참가 물질

5

반응물 3

HCID 517165Ammonium AcetateHCID 9768002-Methoxy-4-morpholin-4-yl-benzaldehydeHCID 89738581HCID 89738581, 화합물

생성물 1

HCID 178493034HCID 178493034, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
70 °C

실험 절차

(1S,2R,3S,4R)-3-(2,3-diamino-5-chloropyridin-4-ylamino)-7-oxabicyclo[2.2.1]heptane-2-carboxamide (17) (140 mg, 0.47 mmol), 2-methoxy-4-morpholinobenzaldehyde (93 mg, 0.42 mmol) were taken in EtOH (15 ml) to which ammonium acetate (40 mg) was added and the reaction mixture was heated at 70° C. for 48 h. Crude LCMS showed the desired product along with trace of starting material. The reaction mixture was allowed to come to rt and the precipitated was filtered and washed well with hot ethanol to afford the desired product (120 mg, 51%) as an off white solid. NMR: δ (1H, 400M Hz, CDCl3): 1.50-1.80 (4H, m), 2.95 (1H, d, J=8.4 Hz), 3.27 (4H, bs), 3.76 (4H, bs), 3.96 (3H, s), 4.32 (1H, d, J=4.4 Hz), 4.57 (1H, s), 5.51 (1H, t, J=4.4 Hz), 6.63 (1H, s), 6.69 (1H, d, J=8.4 Hz), 6.90 (1H, d, J=8.4 Hz), 7.18 (1H, s), 7.60 (1H, s), 7.91 (1H, s), 8.05 (1H, d, J=8.8 Hz), 12.14 (1H, s). LCMS (254 nm): [M+H]+ 499.00 (100%). HPLC: (254 nm) 97.68%.

후처리

  1. additionwas added

출처 및 근거

ORD 기록
ord-cee6396f7451424a9a862d648b843659
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238656B2

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