Hydrochloric Acid → N-[4-[[(2,4-Diaminopyrido[2,3-d]pyrimidin-6-yl)methyl]methylamino]benzoyl]-L-glutamic acid

HRID 370524

反応式

HRID 370524 の反応式
[CH:1]1[C:6]([C:7]([NH:9][C@H:10]([C:16]([OH:18])=[O:17])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:8])=[CH:5][CH:4]=[C:3]([NH:19][CH2:20][C:21]2[CH:26]=[C:25]3[C:27]([NH2:32])=[N:28][C:29]([NH2:31])=[N:30][C:24]3=[N:23][CH:22]=2)[CH:2]=1.[OH-].[Na+].C=O.[BH3-][C:38]#N.[Na+].Cl>O=O>[NH2:31][C:29]1[N:28]=[C:27]([NH2:32])[C:25]2[CH:26]=[C:21]([CH2:20][N:19]([CH3:38])[C:3]3[CH:2]=[CH:1][C:6]([C:7]([NH:9][C@H:10]([C:16]([OH:18])=[O:17])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:8])=[CH:5][CH:4]=3)[CH:22]=[N:23][C:24]=2[N:30]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 972725-DeazaaminopterinHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 12908480N-[4-[[(2,4-Diaminopyrido[2,3-d]pyrimidin-6-yl)methyl]methylamino]benzoyl]-L-glutamic acid

試薬・触媒・溶媒 1

HCID 977Oxygen溶媒

実験手順

A suspension of Compound II (R=H) (100 mg, 0.211 mmol) in O2 free water (5 ml) under N2 was adjusted to pH 6.4 with 1N NaOH to give a solution which was treated with 38% HCHO (83.1 μl, 1.14 mmol) followed by NaBH3CN (19.9 mg, 0.317 mmol). The solution was maintained at pH 6.4 by gradual addition of 1N HCl over a period of 45 minutes. The solution was stirred under N2 for 23 hours, filtered and acidified to pH 3.6 with 1N HCl. The product was collected by filtration, washed with water at pH 3.6 and dried in vacuo (P2O5): yield 97 mg (94%), mp indefinite (softens and darkens above 217° C.); mass spectrum, m/e 454 (M+1)+ ; λmax nm (ε×10-3): 0.1N HCl-221 (37.1), 311 (19.0); pH 7-219 (35.1), 247 (18.1), 305 (25.2); 0.1N NaOH-249 (19.9), 305 (25.0), 355 sh (6.15; 1H-NMR (DMSO-d6, <5% w/v), δ2.00 m (CH2CH2CO), 2.28 t (CH2CO), 3.12 s (CH3), 4.32 m (CHN), 4.66 s (CH2N), 6.78 d, 7.72 d (C6H4), 8.31 d (5-CH), 8.59 d (7-CH).

後処理

  1. customto give a solution which
  2. filtrationfiltered
  3. filtrationThe product was collected by filtration
  4. washwashed with water at pH 3.6
  5. dry with materialdried in vacuo (P2O5)
  6. customyield 97 mg (94%), mp indefinite (softens and darkens above 217° C.)
  7. wait1H-NMR (DMSO-d6, <5% w/v), δ2.00 m (CH2CH2CO), 2.28 t (CH2CO), 3.12 s (CH3), 4.32 m (CHN), 4.66 s (CH2N), 6.78 d, 7.72 d
  8. custom(C6H4), 8.31 d (5-CH), 8.59 d (7-CH)

出典と根拠

ORDレコード
ord-ecc27af279ea41e9bc7154d6d271890f
出典データセット
uspto-grants-1985_07
特許番号
US04526964

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