Ammonium Chloride → HCID 178445911, compound

HRID 1831467Notes

Reaction equation

HRID 1831467 reaction equation
C(=O)=O.CC(C)=O.[NH2:8][C:9]1[S:10][C:11]2[C:16]([NH:17][C@H:18]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:19][OH:20])=[N:15][C:14]([S:25]CC3C=CC=CC=3)=[N:13][C:12]=2[N:33]=1.[Na].[NH4+].[Cl-]>N>[NH2:8][C:9]1[S:10][C:11]2[C:16]([NH:17][C@H:18]([CH2:21][CH:22]([CH3:23])[CH3:24])[CH2:19][OH:20])=[N:15][C:14]([SH:25])=[N:13][C:12]=2[N:33]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 18522661Acetone cardiceHCID 58230405HCID 58230405, compound

Product 1

HCID 178445911HCID 178445911, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

Liquid ammonia (140 mL) was condensed into a 250 mL flask (dry ice/acetone cooling) is and (R)-2-(2-amino-5-phenylmethylthio-thiazolo[4,5-d]pyrimidin-7-ylamino)-4-methyl-pentan-1-ol (WO 00/09511) (2.77 g, 7.11 mmol) was added in three portions. To the clear yellow solution was added an excess of sodium metal in small pieces, until a blue colour persisted. When the blue colour had remained for 25 seconds, solid NH4Cl was added to quench the reaction. The NH3 solvent was removed (N2), and the remains were dissolved in H2O (ca 70 mL), the mixture filtered, and the resulting clear solution neutralized to pH ca 7 with dilute HCl. The precipitated solid was filtered, washed with H2O and CH3CN, and dried at 40° C. under vacuum overnight to give 1.98 g (93%) of a light yellow solid.

Workup

  1. customto quench
  2. customthe reaction
  3. customThe NH3 solvent was removed (N2)
  4. dissolutionthe remains were dissolved in H2O (ca 70 mL)
  5. filtrationthe mixture filtered
  6. filtrationThe precipitated solid was filtered
  7. washwashed with H2O and CH3CN
  8. customdried at 40° C. under vacuum overnight

Sources & evidence

ORD record
ord-a938459657f54136a6a531b20f2c7bfa
Source dataset
uspto-grants-2006_06
Patent number
US07067657B2

Reaction notes

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