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

HRID 1388500노트

반응식

HRID 1388500 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 977Oxygen용매

실험 절차

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 1 N 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 1 N HCl over a period of 45 minutes. The solution was stirred under N2 for 23 hours, filtered and acidified to pH 3.6 with 1 N 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): 0.1 N HCl --221 (37.1), 311 (19.0); pH 7-219 (35.1), 247 (18.1), 305 (25.2); 0.1 N 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).

후처리

  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)

출처 및 근거

ORD 기록
ord-37c48724bb324b099e8b0bb5a56039fb
출처 데이터셋
uspto-grants-1984_02
특허 번호
US04431805

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