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Acetic Acid → Ammonium Hydroxide

HRID 75598
ノート
印刷プレビュー

反応式

HRID 75598 の反応式
C([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[C:21]([NH:22][C:23]([NH:25][C@@H:26]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C@H:29]([O:36][C:37]4[CH:38]=[CH:39][C:40]5[N:41]([C:43]([CH:46]([CH3:48])[CH3:47])=[N:44][N:45]=5)[CH:42]=4)[CH2:28][CH2:27]3)=[O:24])=[CH:20][C:19]([C:49]([CH3:52])([CH3:51])[CH3:50])=[N:18]2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C=O.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[NH4+:11].[OH-:8].[C:49]([C:19]1[CH:20]=[C:21]([NH:22][C:23]([NH:25][C@@H:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C@H:29]([O:36][C:37]3[CH:38]=[CH:39][C:40]4[N:41]([C:43]([CH:46]([CH3:48])[CH3:47])=[N:44][N:45]=4)[CH:42]=3)[CH2:28][CH2:27]2)=[O:24])[N:17]([CH:14]2[CH2:13][CH2:12][N:11]([CH3:9])[CH2:16][CH2:15]2)[N:18]=1)([CH3:52])([CH3:51])[CH3:50]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86686695HCID 86686695、化合物

生成物 2

HCID 14923Ammonium Hydroxide収率 0.1%
HCID 71598646
1-[5-tert-Butyl-2-(1-methyl-piperidin-4-yl)-2H-pyrazol-3-yl]-3-[(1S,4R)-4-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-yl]-urea

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of Example 16 (half crude material, assume 64.8 mg, 0.114 mmol) and formaldehyde (37% in water, 0.092 mL, 1.14 mmol) in DCM (2 mL) was stirred at RT for 10 min, then AcOH (0.013 mL, 0.227 mmol) and NaBH(OAc)3 (48.1 mg, 0.227 mmol) were added sequentially, and the solution stirred at RT for 3 h. The solution was concentrated in vacuo to ˜0.5 mL volume, applied to an SCX-2 cartridge (2 g) and washed with MeOH (15 mL). The product was eluted with 2M NH3 in MeOH (10 mL); concentration in vacuo left a pale yellow solid (82.6 mg). HPLC (XBridge C18, 30-98% MeCN in H2O, 0.1% NH4OH) gave the title compound as a white solid after freeze-drying (30.8 mg, 46%). LCMS (Method 5): Rt 3.18 min, m/z 585 [MH+]. 1H NMR (400 MHz, d6-DMSO): 1.21 (9H, s), 1.38 (H, d, J 6.8), 1.40 (3H, d, J 6.8), 1.75 (2H, t, J 12.2), 1.91-2.04 (6H, m), 2.07-2.17 (2H, m), 2.18 (3H, s), 2.87 (2H, d, J 10.6), 3.58 (1H, sept, J 6.8), 3.88 (1H, m), 4.88 (1H, m), 5.56 (1H, t, J 4.7), 6.02 (1H, s), 6.89 (1H, d, J 8.6), 7.19 (1H, dd, J 9.8, 2.1), 7.31 (1H, m), 7.36-7.43 (3H, m), 7.70 (1H, d, J 9.8), 8.06 (1H, s), 8.22 (1H, d, J 2.0).

後処理

  1. concentrationThe solution was concentrated in vacuo to ˜0.5 mL volume
  2. washwashed with MeOH (15 mL)
  3. washThe product was eluted with 2M NH3 in MeOH (10 mL)
  4. concentrationconcentration in vacuo
  5. waitleft a pale yellow solid (82.6 mg)

出典と根拠

ORDレコード
ord-ecfa033410c84a599f9bb528277c35d3
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08835431B2

反応ノート

読み込み中…

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