4-Morpholinobenzaldehyde → HCID 178514001, 화합물

HRID 592058노트

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HRID 592058 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.[O:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=2)[CH2:23][CH2:22]1.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:31]([C:30]3[CH:29]=[CH:28][C:27]([N:24]4[CH2:25][CH2:26][O:21][CH2:22][CH2:23]4)=[CH:34][CH:33]=3)[NH:1][C:2]2=[N:3][CH:4]=1

참가 물질

5

반응물 3

HCID 2913494-MorpholinobenzaldehydeHCID 517165Ammonium AcetateHCID 89738581HCID 89738581, 화합물

생성물 1

HCID 178514001HCID 178514001, 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) (300 mg, 0.971 mmol), and 4-morpholinobenzaldehyde (167 mg, 0.873 mmol) were taken in EtOH (15 ml) to which ammonium acetate (112 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 (466 mg, 23%) as a yellow solid. NMR: δ (1H, 400M Hz, DMSO-d6): 1.50-1.80 (4H, m), 2.96 (1H, d, J=8.4 Hz), 3.23 (4H, s), 3.76 (4H, s), 4.33 (1H, d, J=4.5 Hz), 4.57 (1H, s), 5.49 (1H, t, J=8.8 Hz), 6.99 (1H, d, J=8.4 Hz), 7.08 (1H, d, J=8.4 Hz), 7.18 (1H, s), 7.62 (1H, s), 7.91 (1H, s), 8.02 (1H, d, J=8.0 Hz), 12.96 (1H, s). LCMS (254 nm): [M+H]+ 469.15 (95.56%) HPLC: 91.64% (220 nm).

후처리

  1. additionwas added

출처 및 근거

ORD 기록
ord-c2e42a71a30441a5a12af7c455735f53
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238656B2

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