Sodium Bicarbonate → HCID 59232198, compound

HRID 1099304Notes

Reaction equation

HRID 1099304 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]([OH:13])=O)[N:6]2[N:5]=[CH:4][N:3]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[NH2:37][CH2:38][CH:39]1[O:44][CH2:43][CH2:42][N:41]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:40]1.C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]([NH:37][CH2:38][CH:39]3[O:44][CH2:43][CH2:42][N:41]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:40]3)=[O:13])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

7

Reactant 5

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 19081094tert-Butyl 2-(aminomethyl)morpholine-4-carboxylateHCID 59231956HCID 59231956, compound

Product 1

HCID 59232198HCID 59232198, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-aminopyrrolo[2,1-f][1,2,4]triazine-7-carboxylic acid (215 mg, 1.21 mmol) was combined with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (347 mg, 1.81 mmol) and 1-hydroxybenzotriazole monohydrate (245 mg, 1.81 mmol) in DMF (5 mL). The mixture was stirred at rt for 30 min. before adding tert-butyl 2-(aminomethyl)morpholine-4-carboxylate (274 mg, 1.27 mmol). After 1 hr, the reaction was poured into satd. NaHCO3 solution and stirred for 1 h. The product was collected by vacuum filtration to give a tan solid (400 mg, 88%). MS [M+H]+=377.0; LCMS RT=2.71 min.

Workup

  1. waitAfter 1 hr
  2. additionthe reaction was poured into satd
  3. filtrationThe product was collected by vacuum filtration

Sources & evidence

ORD record
ord-0eabac1a7382495088c2bfa31028adf9
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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